dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cddf8b0bbaa34d7fad426cd90b95c72f | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>>CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | C1COCCN1C2=CC(=O)N3C=CC=C(C3=N2)C4=CC=CC5=C4SC6=C5C=C(C=C6)OS(=O)(=O)C(F)(F)F.CNC(=O)CN1CCOCC1>>CN(C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6)C(=O)CN7CCOCC7 | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.O=S(=O)(O[c:12]1[cH:13][cH:14][c:15]2[s:16][c:17]3[c:18](-[c:19]4[cH:20][cH:21][cH:22][n:23]5[c:24](=[O:25])[cH:26][c:27]([N:28]6[CH2:29][CH2:30][O:31][CH2:32][CH2:33]6)[n:34][c:35]45)[cH:36][cH:37][cH:38][c:39]3[c:40]2[cH:41]1)C(F)(F)F>>[CH3:1... | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12 | CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Alkylation of amines | e52425da26c6d807074f7b38f990dc0bf487f798ff5c4971b6b28c7848a26596 | e8f1037ddf00c3008e109a885e9239c96953665a705783a27060bdf402b979e6 | O=C(CN1CCOCC1)Nc1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1.[C:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C;D1;H3:12]>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C:9](-[C:8])=[O;D1;H0:10]):[c:7]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CN(C1=CC2=C(C=C1)SC3=C2C=CC=C3C4=CC=CN5C4=NC(=CC5=O)N6CCOCC6)C(=O)CN7CCOCC7", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a microwave vial, under nitrogen, at room temperature, a solution of 6-(2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (63 mg, 0.11 mmol) in dry toluene (1 mL) was added to a stirred mixture of N-methyl-2-morpholinoacetamide (35.5 mg, 0.22 mmol), Tripotassium ph... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Triflate.Secondary amide | Tertiary amide | c1ccc2c(c1)sc1ccccc12 | c1ccc2c(c1)sc1ccccc12 | C1COCC[NH]1.c1ccn2ccccc2n1.C1COCC[NH]1.c1ccc2c(c1)sc1ccccc12 | TfOH.HO- | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | CNC(=O)CN1CCOCC1.O=c1cc(N2CCOCC2)nc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccn12>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CN(C(=O)CN1CCOCC1)c1ccc2sc3c(-c4cccn5c(=O)cc(N6CCOCC6)nc45)cccc3c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-086118e3608c416e9d858ba54c5d1e17 | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3c(C)cc(Cl)nc3O2)n1>>COc1nc(Nc2cc(C)c3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CC(=NC2=C1CN(CC(O2)C3=NC(=CS3)C)C)Cl.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CC(=NC2=C1CN(CC(O2)C3=NC(=CS3)C)C)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[c:29]1[cH:30][n:31][n:32]([CH3:33])[cH:34]1.Cl[c:7]1[cH:8][c:9]([CH3:10])[c:11]2[c:12]([n:13]1)[O:14][CH:15]([c:16]1[n:17][c:18]([CH3:19])[cH:20][s:21]1)[CH2:22][N:23]([CH3:24])[CH2:25]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]3[c:... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3c(C)cc(Cl)nc3O2)n1 | COc1nc(Nc2cc(C)c3c(n2)OC(c2nc(C)cs2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1csc(C2CNCc3ccc(Nc4ccc(-c5cn[nH]c5)cn4)nc3O2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 22.86 | [{"value": 22.86, "product": "CC1=CC(=NC2=C1CN(CC(O2)C3=NC(=CS3)C)C)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4,6-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (185 mg, 0.60 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (122 mg, 0.60 mmol), Pd2dba3 (13.67 mg, 0.01 mmol), BINAP (18.59 mg, 0.03 mmol) and SODIUM TERT-BUTOXIDE (92 mg, 0.96 mmol) were weighed into a microwav... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1cscn1.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2CN(C)Cc3c(C)cc(Cl)nc3O2)n1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CO... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-96727602adb24b28af9c737e24f7315c | CC(=O)Nc1cnc(Br)cn1.CN1CCNCC1>>CC(=O)Nc1cnc(N2CCN(C)CC2)cn1 | CC(=O)NC1=CN=C(C=N1)Br.CN1CCNCC1>>CC(=O)NC1=CN=C(C=N1)N2CCN(CC2)C | Br[c:8]1[n:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:17][cH:16]1.[NH:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][n:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]2)[cH:16][n:17]1 | CC(=O)Nc1cnc(Br)cn1.CN1CCNCC1 | CC(=O)Nc1cnc(N2CCN(C)CC2)cn1 | CC(C)(C)[O-].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a752b8271b175119ca80c4ec7eb95ecc759b3641e02647044be70538f5c2e04a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[C:11]-[C:12]-1 | 79.51 | [{"value": 79.51, "product": "CC(=O)NC1=CN=C(C=N1)N2CCN(CC2)C", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | 1-methylpiperazine (2.318 g, 23.14 mmol), N-(5-bromopyrazin-2-yl)acetamide (1 g, 4.63 mmol), tri-tert-butylphosphine (1.873 g, 9.26 mmol), tris(dibenzylideneacetone)dipalladium (0.085 g, 0.09 mmol) and potassium 2-methylpropan-2-olate (1.039 g, 9.26 mmol) were suspended in DMF (9.26 ml) and sealed into a microwave tube... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1cnccn1.C1CNCC[NH]1 | c1cnccn1.C1C[NH]CC[NH]1 | c1cnccn1.C1C[NH]CC[NH]1 | HBr | CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O | 120 | null | CC(=O)Nc1cnc(Br)cn1.CN1CCNCC1>CC(C)(C)[O-].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN(C)C=O>CC(=O)Nc1cnc(N2CCN(C)CC2)cn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3c36e457f5e64b5b9130db89ea6a541e | Clc1ccnc(Cl)c1.Nc1cccnc1>>Clc1ccnc(Nc2cccnc2)c1 | C1=CN=C(C=C1Cl)Cl.C1=CC(=CN=C1)N>>C1=CC(=CN=C1)NC2=NC=CC(=C2)Cl | Cl[c:6]1[n:5][cH:4][cH:3][c:2]([Cl:1])[cH:14]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[cH:14]1 | Clc1ccnc(Cl)c1.Nc1cccnc1 | Clc1ccnc(Nc2cccnc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccnc2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[c:9]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:8] | 51.48 | [{"value": 51.48, "product": "C1=CC(=CN=C1)NC2=NC=CC(=C2)Cl", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | pyridin-3-amine (95 mg, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | Clc1ccnc(Cl)c1.Nc1cccnc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1ccnc(Nc2cccnc2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b9b3987212a34b6286e3f0f13f180d9b | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(C1CCCO1)O2>>COc1nc(Nc2cc(C)c3c(n2)OC(C2CCCO2)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CC(=NC2=C1CN(CC(O2)C3CCCO3)C)Cl.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CC(=NC2=C1CN(CC(O2)C3CCCO3)C)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[c:28]1[cH:29][n:30][n:31]([CH3:32])[cH:33]1.Cl[c:7]1[cH:8][c:9]([CH3:10])[c:11]2[c:12]([n:13]1)[O:14][CH:15]([CH:16]1[CH2:17][CH2:18][CH2:19][O:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]3[c:12](... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(C1CCCO1)O2 | COc1nc(Nc2cc(C)c3c(n2)OC(C2CCCO2)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OC(C2CCCO2)CNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 35.51 | [{"value": 35.51, "product": "CC1=CC(=NC2=C1CN(CC(O2)C3CCCO3)C)NC4=NC(=C(C=C4)C5=CN(N=C5)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (205 mg, 1.00 mmol), Pd2(dba)3 (22.99 mg, 0.03 mmol), BINAP (31.3 mg, 0.05 mmol) and SODIUM TERT- BUTOXIDE (193 mg, 2.01 mmol) were placed in a round bottomed flask. The flask was stoppered with a septum and flushed with argon. To this was added a solution of 8-chlo... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.C1CCOC1.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(C1CCCO1)O2>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1n... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a7f71cce88db46cba0388c01927b5a88 | CCOC(=O)c1cc(=O)c2cc(OC)cc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc(=O)c2cc(OC)cc(N3CCN(Cc4ccccc4)CC3)c2o1 | CCOC(=O)C1=CC(=O)C2=C(O1)C(=CC(=C2)OC)Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC(=O)C2=C(O1)C(=CC(=C2)OC)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:16]1[cH:15][c:12]([O:13][CH3:14])[cH:11][c:10]2[c:8](=[O:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:31][c:30]21.[NH:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](=[O:9])[c:10]2[cH:11][c:12]([O:13][CH3:14])... | CCOC(=O)c1cc(=O)c2cc(OC)cc(Br)c2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc(=O)c2cc(OC)cc(N3CCN(Cc4ccccc4)CC3)c2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3e03860baad0175cfb4d8b8e802db1a1d01a3b5f436d5a117480c14a79f3a356 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccoc2c(N3CCN(Cc4ccccc4)CC3)cccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7]-[C:8](-[#8:9])=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]:[#8;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[c:2]:[c:3] | 48.39 | [{"value": 48.39, "product": "CCOC(=O)C1=CC(=O)C2=C(O1)C(=CC(=C2)OC)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Tris(dibenzylideneacetone)dipalladium(0) (0.280 g, 0.31 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.457 g, 0.73 mmol), ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate (2 g, 6.11 mmol), 1-benzylpiperazine (1.169 mL, 6.73 mmol) and cesium carbonate (2.79 g, 8.56 mmol) were heated under argon to 80 °C in... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occcc2c1.C1CNCC[NH]1 | c1ccc2occcc2c1.C1C[NH]CC[NH]1 | c1ccc2occcc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 80 | null | CCOC(=O)c1cc(=O)c2cc(OC)cc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2683b0f554e64a9e9de3f6ed71e783e9 | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC(C)(C)C>>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC(C)(C)C | CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)Br.C1COCCN1>>CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)N2CCOCC2 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:14]([NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:12]([CH3:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21... | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC(C)(C)C | Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC(C)(C)C | CC(C)(C)[O-].[K+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 63.67 | [{"value": 63.67, "product": "CC1=CC(=CC(=C1NC(=O)CC(C)(C)C)C)N2CCOCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Exemplar cmpd from , though employing slightly different Buchwald-Hartwig coupling conditions. Tris(dibenzylidenacetone)dipalladium(0) (31 mg, 0.03 mmol) and 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (27 mg, 0.07 mmol) were stirred in anhydrous toluene (3 mL) for 15 minutes under an argon (g) sparge. To ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[K+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 80 | null | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC(C)(C)C>CC(C)(C)[O-].[K+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC(C)(C)C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-25b2f8bfafe540368db659a4bd1935bf | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1>>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 | CC1=CC(=CC(=C1NC(=O)CC2CCCC2)C)Br.C1COCCN1>>CC1=CC(=CC(=C1NC(=O)CC2CCCC2)C)N3CCOCC3 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:14]([NH:15][C:16](=[O:17])[CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[c:12]([CH3:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([CH3:13])[c:14]1[NH:15][C:16](=[O:17])[CH2:18][CH:19]1[CH2:20][... | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1 | Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 | CC(C)(C)[O-].[K+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(CC1CCCC1)Nc1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | 13.21 | [{"value": 13.21, "product": "CC1=CC(=CC(=C1NC(=O)CC2CCCC2)C)N3CCOCC3", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Exemplar cmpd from, though employing slightly different Buchwald-Hartwig coupling conditions. Tris(dibenzylidenacetone)dipalladium(0) (31 mg, 0.03 mmol) and 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (27 mg, 0.07 mmol) were stirred in anhydrous toluene (3 mL) for 15 minutes under an argon (g) sparge. To t... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.C1CCCC1 | HBr | CC(C)(C)[O-].[K+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 80 | null | C1COCCN1.Cc1cc(Br)cc(C)c1NC(=O)CC1CCCC1>CC(C)(C)[O-].[K+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-80551a125bb34e24a0d215f47bcdf5d9 | COc1cc(Br)ccc1OCc1ccccc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>COc1cc(N2CCN[C@H](C)C2)ccc1OCc1ccccc1 | COC1=C(C=CC(=C1)Br)OCC2=CC=CC=C2.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>>C[C@@H]1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)OC | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:14][cH:13]1.CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][NH:6][CH2:12][C@H:10]1[CH3:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][C@H:10]([CH3:11])[CH2:12]2)[cH:13][cH:14][c:15]1[O:16][CH2:17][c:18]1[cH:19][cH:20... | COc1cc(Br)ccc1OCc1ccccc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C | COc1cc(N2CCN[C@H](C)C2)ccc1OCc1ccccc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 1155a782af40ddd9c7c7ab45b40bc8450f26a553a41c0f0d5dfec075d80a69f3 | 4692e9cfac8ca0f49eb5c33838ae1fa5c1a375a44556f0da8885d569da661aa1 | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1-[C;D1;H3:12]>>[C;D1;H3:12]-[C:11]1-[C:10]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8]-[C:7]-[NH;D2;+0:6]-1 | 40.26 | [{"value": 40.26, "product": "C[C@@H]1CN(CCN1)C2=CC(=C(C=C2)OCC3=CC=CC=C3)OC", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To (R)-tert-butyl 2-methylpiperazine-1-carboxylate (0.717 g, 3.58 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.094 g, 0.10 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.085 g, 0.14 mmol) and Sodium tert-butoxide (0.459 g, 4.78 mmol) was added a solution of 1-(benzyloxy)-4-bromo-2-methoxybenzene (1 g, 3... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 80 | null | COc1cc(Br)ccc1OCc1ccccc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc1cc(N2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9a60950bdd244f9f856c1f63589f5d48 | CCONC(=O)c1ccccc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CCONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.CCONC(=O)C1=CC=CC=C1N>>CCONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CC(=NN3C)C | [CH3:1][CH2:2][O:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([NH:17][c:18]2[cH:19][c:20]([CH3:21])[n:22][n:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][CH2:2][O:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16... | CCONC(=O)c1ccccc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CCONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 74.48 | [{"value": 74.48, "product": "CCONC(=O)C1=CC=CC=C1NC2=CC(=NC=C2C(F)(F)F)NC3=CC(=NN3C)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), 2-amino-N-ethoxybenzamide (120 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were weighed ou... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CCONC(=O)c1ccccc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CCONC(=O)c1ccccc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-84fa8d5c5cab44cab16622511b581f38 | Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1.Nc1ccccc1C(=O)NOCCO>>Cc1cc(Nc2cc(Nc3ccccc3C(=O)NOCCO)c(C(F)(F)F)cn2)n(C)n1 | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.C1=CC=C(C(=C1)C(=O)NOCCO)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOCCO)C(F)(F)F)C | I[c:8]1[cH:7][c:6]([NH:5][c:4]2[cH:3][c:2]([CH3:1])[n:32][n:30]2[CH3:31])[n:29][cH:28][c:23]1[C:24]([F:25])([F:26])[F:27].[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16](=[O:17])[NH:18][O:19][CH2:20][CH2:21][OH:22]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]... | Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1.Nc1ccccc1C(=O)NOCCO | Cc1cc(Nc2cc(Nc3ccccc3C(=O)NOCCO)c(C(F)(F)F)cn2)n(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[... | 48.64 | [{"value": 48.64, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOCCO)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (22.71 mg, 0.04 mmol), diacetoxypalladium (4.41 mg, 0.02 mmol), 2-amino-N-(2-hydroxyethoxy)benzamide (131 mg, 0.67 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (150 mg, 0.39 mmol) and cesium carbonate (256 mg, 0.79 mmol) were... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]n1.c1ccncc1.c1ccccc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1.Nc1ccccc1C(=O)NOCCO>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1cc(Nc2cc(Nc3ccccc3C(=O)NOCCO)c(C(F)(F)F)cn2)n(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7b17e577dfcd4694a98108d8e01246cd | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=CC=C(C=C2)N>>CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:11]1[cH:12][cH:13][c:14]2[c:15]([n:16]1)[O:17][C@H:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][N:26]([CH3:27])[CH2:28]2.[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[n:31]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1 | Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), 2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1nnc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b07c6adf9728420aa254eb2e3d6b36f4 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=CC=C(C=C2)N>>CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:11]1[cH:12][cH:13][c:14]2[c:15]([n:16]1)[O:17][C@H:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][N:26]([CH3:27])[CH2:28]2.[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[n:31]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1 | Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), 2-(DICYCLOHEXYLPHOS... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1nnc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-22e3f80de08948fdaf8c37b04b642dc6 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=CC=C(C=C2)N>>CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:11]1[cH:12][cH:13][c:14]2[c:15]([n:16]1)[O:17][C@H:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][N:26]([CH3:27])[CH2:28]2.[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[n:31]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1 | Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CC(C)(C)[O-].[K+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (0.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), 2-(DICYCLOHEXYLPHO... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1nnc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-221a1c88a71944db90ec733265031251 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=CC=C(C=C2)N>>CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:11]1[cH:12][cH:13][c:14]2[c:15]([n:16]1)[O:17][C@H:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][N:26]([CH3:27])[CH2:28]2.[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[n:31]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1 | Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), XANTPHOS (1.053 mg,... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1nnc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8f9b18030951427ab1e1a3e32247196d | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=CC=C(C=C2)N>>CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3 | Cl[c:11]1[cH:12][cH:13][c:14]2[c:15]([n:16]1)[O:17][C@H:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:25][N:26]([CH3:27])[CH2:28]2.[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[n:31]1>>[CH3:1][c:2]1[n:3][cH:4][n:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]4[c:... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1 | Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=NN(C=N1)C2=CC=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (.5 mL) was added via a syringe to a capped microwave vial containing Pd2(dba)3 (0.833 mg, 0.91 µmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHEN... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1nnc[nH]1.c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-dc56e46e611f4db1889616d29baeeb5f | C1CNCCN1.NC(=O)c1cc2c(Br)cccc2o1>>NC(=O)c1cc2c(N3CCNCC3)cccc2o1 | C1=CC2=C(C=C(O2)C(=O)N)C(=C1)Br.C1CNCCN1>>C1CN(CCN1)C2=C3C=C(OC3=CC=C2)C(=O)N | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Br[c:7]1[c:6]2[cH:5][c:4]([C:2]([NH2:1])=[O:3])[o:18][c:17]2[cH:16][cH:15][cH:14]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[c:7]([N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[cH:14][cH:15][cH:16][c:17]2[o:18]1 | C1CNCCN1.NC(=O)c1cc2c(Br)cccc2o1 | NC(=O)c1cc2c(N3CCNCC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 986e7e7b1534fb66a44c60729b3e695d082f73e7dc2085e2caae38d8f1c52b11 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2ccoc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[N;D1;H2:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[N;D1;H2:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:17]-[C:18]-[#7:13]-[C:14]-[C:15]-3):[c:12]:2... | 0 | [{"value": 0.0, "product": "C1CN(CCN1)C2=C3C=C(OC3=CC=C2)C(=O)N", "details": "", "is_desired": true}] | 70 | CELSIUS | null | null | The crude product from EN03731-54-001, 4-bromobenzofuran-2-carboxamide (0.600 g, 2.5 mmol), was dissolved in THF (18 mL) and water (18.00 mL). To this mixture were added piperazine (1.077 g, 12.50 mmol), Cesium carbonate (1.629 g, 5.00 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.114 g, 0.13 mmol) and rac-2,2'-Bi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2occc2c1 | C1C[NH]CCN1.c1ccc2occc2c1 | C1C[NH]CCN1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | 70 | null | C1CNCCN1.NC(=O)c1cc2c(Br)cccc2o1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1>NC(=O)c1cc2c(N3CCNCC3)cccc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-100bcab4f1bd45d89d76662307487cf4 | CC(C)(C)OC(=O)N1CCNCC1.Cc1cccc(Br)c1[N+](=O)[O-]>>Cc1cccc(N2CCN(C(=O)OC(C)(C)C)CC2)c1[N+](=O)[O-] | CC1=C(C(=CC=C1)Br)[N+](=O)[O-].CC(C)(C)OC(=O)N1CCNCC1>>CC1=C(C(=CC=C1)N2CCN(CC2)C(=O)OC(C)(C)C)[N+](=O)[O-] | [NH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.Br[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:20]1[N+:21](=[O:22])[O-:23]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]2)[c:20]1[... | CC(C)(C)OC(=O)N1CCNCC1.Cc1cccc(Br)c1[N+](=O)[O-] | Cc1cccc(N2CCN(C(=O)OC(C)(C)C)CC2)c1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 16.81 | [{"value": 16.81, "product": "CC1=C(C(=CC=C1)N2CCN(CC2)C(=O)OC(C)(C)C)[N+](=O)[O-]", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | tert-butyl piperazine-1-carboxylate (172 mg, 0.93 mmol) and 1-bromo-3-methyl-2-nitrobenzene (0.124 mL, 0.93 mmol), were added to a stirred solution of diacetoxypalladium (20.78 mg, 0.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (107 mg, 0.19 mmol) and cesium carbonate (664 mg, 2.04 mmol) dissolve... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | CC(C)(C)OC(=O)N1CCNCC1.Cc1cccc(Br)c1[N+](=O)[O-]>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Cc1cccc(N2CCN(C(=O)OC(C)(C)C)CC2)c1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-41642501237541609124229452d981cb | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F>>CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 | C1=CC(=C(C=C1Br)F)C=O.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CC(=C(C=C1)C=O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8].Br[c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[c:15]([F:16])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[c:15]([F:16])[cH:17]1 | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F | CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 6908f1dcf5268c746b7a7269b75335bd2fc1b14f2d985976d054ac2fda336d3a | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 83.59 | [{"value": 83.59, "product": "CC(C)(C)OC(=O)NC1=CC(=C(C=C1)C=O)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of 4-bromo-2-fluorobenzaldehyde (0.670 g, 3.30 mmol) dissolved in toluene (10 mL) was treated with tert-butyl carbamate (0.464 g, 3.96 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.164 g, 0.26 mmol), Bis(dibenzylideneacetone)palladium (0.076 g, 0.13 mmol) and cesium carbonate (1.527 g, 4.69 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-122adeafa04f44969e42186d0dc6c6bd | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F>>CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 | C1=CC(=C(C=C1Br)F)C=O.CC(C)(C)OC(=O)N>>CC(C)(C)OC(=O)NC1=CC(=C(C=C1)C=O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH2:8].Br[c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[c:15]([F:16])[cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[c:15]([F:16])[cH:17]1 | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F | CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 6908f1dcf5268c746b7a7269b75335bd2fc1b14f2d985976d054ac2fda336d3a | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:13])-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 97.47 | [{"value": 97.47, "product": "CC(C)(C)OC(=O)NC1=CC(=C(C=C1)C=O)F", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | A solution of 4-bromo-2-fluorobenzaldehyde (3.09 g, 15.22 mmol) dissolved in toluene (40 mL) was treated with tert-butyl carbamate (2.140 g, 18.27 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.758 g, 1.22 mmol), Bis(dibenzylideneacetone)palladium (0.350 g, 0.61 mmol) and cesium carbonate (7.04 g, 21.62 mmol... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Carbamic ester | Carbamic ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1 | 100 | null | CC(C)(C)OC(N)=O.O=Cc1ccc(Br)cc1F>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)Nc1ccc(C=O)c(F)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-cc832050b1854993a53bbd02bde64312 | CC(C)(C)OC(=O)NCCC1CCNCC1.Ic1ccccc1>>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 | C1=CC=C(C=C1)I.CC(C)(C)OC(=O)NCCC1CCNCC1>>CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=CC=CC=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][NH:14][CH2:21][CH2:22]1.I[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2... | CC(C)(C)OC(=O)NCCC1CCNCC1.Ic1ccccc1 | CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 | [O-]P(=O)([O-])[O-].[K+].[K+].[K+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=CC=CC=C2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of tert-butyl 2-(piperidin-4-yl)ethylcarbamate (0.342 g, 1.5 mmol) in anhydrous DME were added iodobenzene (0.444 g, 2.18 mmol), bis(tri-t- butylphosphine)palladium(0) (0.077 g, 0.15 mmol) and potassium phosphate (0.245 mL, 3.00 mmol). The reaction was heated to 100°C overnight. This reaction did not work... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HI | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].COCCOC | 100 | null | CC(C)(C)OC(=O)NCCC1CCNCC1.Ic1ccccc1>[O-]P(=O)([O-])[O-].[K+].[K+].[K+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd].COCCOC>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f1c56ffe105843279dcf3ce82ed9a4b2 | CN(C)C(=O)c1cc2cccc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>>CN(C)C(=O)c1cc2cccc(N3CCN(Cc4ccccc4)CC3)c2o1 | CN(C)C(=O)C1=CC2=C(O1)C(=CC=C2)Br.C1CN(CCN1)CC2=CC=CC=C2>>CN(C)C(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:12]1[cH:11][cH:10][cH:9][c:8]2[cH:7][c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[o:27][c:26]21.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][N:16]([CH2:17][c:1... | CN(C)C(=O)c1cc2cccc(Br)c2o1.c1ccc(CN2CCNCC2)cc1 | CN(C)C(=O)c1cc2cccc(N3CCN(Cc4ccccc4)CC3)c2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4ccoc34)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7]-[C:8](-[#7:9])=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#7:9]-[C:8](=[O;D1;H0:10])-[c:7]:[#8;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[c:2]:[c:3] | 52.15 | [{"value": 52.15, "product": "CN(C)C(=O)C1=CC2=C(O1)C(=CC=C2)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | The mixture of Tris(dibenzylideneacetone)dipalladium(0) (0.222 g, 0.24 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.231 g, 0.48 mmol) in dioxane (10 mL) (degassed with argon for 5 min) was heated at 95 °C under argon for 5 min . This was transferred to a flask containing 7-bromo-N,N-dimeth... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1 | c1ccc2occc2c1.C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CN(C)C(=O)c1cc2cccc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CN(C)C(=O)c1cc2cccc(N3CCN(Cc4ccccc4)CC3)c2... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-59ade4a657944ddaa87cf04392b14d28 | Brc1ccccc1.CC(C)(C)OC(=O)NCCC1CCNCC1>>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 | C1=CC=C(C=C1)Br.CC(C)(C)OC(=O)NCCC1CCNCC1>>CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=CC=CC=C2 | Br[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][NH:14][CH2:21][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH... | Brc1ccccc1.CC(C)(C)OC(=O)NCCC1CCNCC1 | CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 | CC(C)(C)[O-].[Na+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)NCCC1CCN(CC1)C2=CC=CC=C2", "details": "", "is_desired": true}] | 50 | CELSIUS | null | null | palladium(II) acetate (21.45 mg, 0.10 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (111 mg, 0.19 mmol) were placed in a round-bottomed vessel that was filled with nitrogen. Toluene (0.8 mL) was added and the mixture was heated to 50°C for 30 min. sodium tert-butoxide (138 mg, 1.43 mmol) was adde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | C1CC[NH]CC1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HBr | CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 50 | null | Brc1ccccc1.CC(C)(C)OC(=O)NCCC1CCNCC1>CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)NCCC1CCN(c2ccccc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8cfc6888cfb048a3bbd7a788345f4499 | Brc1cccc2ccoc12.c1ccc(CCN2CCNCC2)cc1>>c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)cc1 | C1=CC2=C(C(=C1)Br)OC=C2.C1CN(CCN1)CCC2=CC=CC=C2>>C1CN(CCN1CCC2=CC=CC=C2)C3=CC=CC4=C3OC=C4 | Br[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][o:18][c:19]12.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]2)[cH:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][CH2:6][N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[cH:16][cH:17][o:18][c:19]34)[CH2:20][CH2:21]2)[cH:2... | Brc1cccc2ccoc12.c1ccc(CCN2CCNCC2)cc1 | c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)cc1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 84c7e95dd5322b5539d35672e86e91fe517bc82d3c61ab206c2baa800dbd5b66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CCN2CCN(c3cccc4ccoc34)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1):[c:4](:[c:5]):[#8;a:6]:[c:7] | 62.12 | [{"value": 62.12, "product": "C1CN(CCN1CCC2=CC=CC=C2)C3=CC=CC4=C3OC=C4", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | A dried Radley tube was charged with rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (6.32 mg, 10.15 µmol), Tris(dibenzylideneacetone)dipalladium(0) (4.65 mg, 5.08 µmol) and Sodium tert- butoxide (34.1 mg, 0.36 mmol). Argon atmosphere was introduced and toluene (3ml) was added followed by 7-bromobenzofuran (50mg, 0.25 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | Brc1cccc2ccoc12.c1ccc(CCN2CCNCC2)cc1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>c1ccc(CCN2CCN(c3cccc4ccoc3... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fb5c3a40f09e4b5fab2cf5db4493aed4 | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1>>COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].C[C@@H]1CNC[C@@H](N1)C>>C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([N+:17](=[O:18])[O-:19])[cH:15]1.[NH:7]1[CH2:8][C@H:9]([CH3:10])[NH:11][C@H:12]([CH3:13])[CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][C@@H:9]([CH3:10])[NH:11][C@@H:12]([CH3:13])[CH2:14]2)[cH:15][c:16]1[N+:17](=[O:18])[O-:19] | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1 | COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 55.97 | [{"value": 55.97, "product": "C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of 4-bromo-1-methoxy-2-nitrobenzene (150 mg, 0.65 mmol) in dioxane (4 mL) was added (2R,6S)-2,6-dimethylpiperazine (221 mg, 1.94 mmol) followed by cesium carbonate (316 mg, 0.97 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (56.4 mg, 0.09 mmol) and diacetoxypalladium (14.51 mg, 0.06 mmol). The result... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5dbc6ee86ad94d33b87d1fb77112c522 | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1>>COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] | COC1=C(C=C(C=C1)Br)[N+](=O)[O-].C[C@@H]1CNC[C@@H](N1)C>>C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-] | Br[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]([N+:17](=[O:18])[O-:19])[cH:15]1.[NH:7]1[CH2:8][C@H:9]([CH3:10])[NH:11][C@H:12]([CH3:13])[CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][C@@H:9]([CH3:10])[NH:11][C@@H:12]([CH3:13])[CH2:14]2)[cH:15][c:16]1[N+:17](=[O:18])[O-:19] | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1 | COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 89.79 | [{"value": 89.79, "product": "C[C@@H]1CN(C[C@@H](N1)C)C2=CC(=C(C=C2)OC)[N+](=O)[O-]", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | To a solution of 4-bromo-1-methoxy-2-nitrobenzene (1500 mg, 6.46 mmol) in dioxane (40 mL) was added (2R,6S)-2,6-dimethylpiperazine (2215 mg, 19.39 mmol) followed by cesium carbonate (3159 mg, 9.70 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (564 mg, 0.91 mmol) and diacetoxypalladium (145 mg, 0.65 mmol). The resu... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCCN1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | COc1ccc(Br)cc1[N+](=O)[O-].C[C@@H]1CNC[C@H](C)N1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc(N2C[C@@H](C)N[C@@H](C)C2)cc1[N+](=O)[O-] |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ffcc436f225c440ca5c8c1a40df255a3 | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC.Cc1cc(N)n(C)n1>>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CNC(=O)C1=C(C=CC=C1OC)NC2=CC(=NC=C2C(F)(F)F)Cl.CC1=NN(C(=C1)N)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C | Cl[c:10]1[cH:9][c:8]([NH:7][c:6]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:29]([O:30][CH3:31])[cH:28][cH:27][cH:26]2)[c:21]([C:22]([F:23])([F:24])[F:25])[cH:20][n:19]1.[NH2:11][c:12]1[cH:13][c:14]([CH3:15])[n:16][n:17]1[CH3:18]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10]([NH:11][c:12]3[cH:13][c:14]([CH3:1... | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC.Cc1cc(N)n(C)n1 | CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 44 | [{"value": 44.0, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | _2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-6-methoxy-N-methylbenzamide (1.66 g, 4.61 mmol)_ _,_ _1,3-dimethyl-1H-pyrazol-5-amine (0.523 g, 4.71 mmol)_ _,_ _diacetoxypalladium (0.083 g, 0.37 mmol)_ _,_ _(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.427 g, 0.74 mmol)_ _and_ _cesium carbonate (1.804... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1c(Nc2cc(Cl)ncc2C(F)(F)F)cccc1OC.Cc1cc(N)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b387923b7ccc41128cba74368ffb7dd0 | CC(C)OCC1CN(C)Cc2ccc(Cl)nc2O1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C)C3)ccc1-n1cnc(C)c1 | CC(C)OCC1CN(CC2=C(O1)N=C(C=C2)Cl)C.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][O:16][CH:17]([CH3:18])[CH3:19])[CH2:20][N:21]([CH3:22])[CH2:23]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:24][cH:25][c:26]1-[n:27]1[cH:28][n:29][c:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][C... | CC(C)OCC1CN(C)Cc2ccc(Cl)nc2O1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OCCNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 5.28 | [{"value": 5.28, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-2-(isopropoxymethyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.157 g, 0.58 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.118 g, 0.58 mmol), Palladium acetate (0.013 g, 0.06 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.020 g, 0.06 mmol) and Cesium carbonate (0.567 g, 1.74 mmol) were pl... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CC(C)OCC1CN(C)Cc2ccc(Cl)nc2O1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f1632d43480c447bab6a25aa93c74396 | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)n1>>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)n1 | CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[n:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:1... | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)n1 | COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | CCO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 18.97 | [{"value": 18.97, "product": "CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (180 mg, 0,66 mmol), 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (134 mg, 0,66 mmol), Palladium acetate (14,71 mg, 0,07 mmol), 2-(Dicyclohexylphosphino)biphenyl (22,96 mg, 0,07 mmol) and Cesium carbonate (640 mg, 1,97 mmol) were mixed ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1nc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].CCO | 100 | null | CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].CCO>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3db391e974974fdaa88ec87b15c89118 | CONC(=O)c1ccccc1N.Cc1nn(C)c(C)c1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1ccccc1Nc1cc(Nc2c(C)nn(C)c2C)ncc1C(F)(F)F | CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)I)C(F)(F)F.CONC(=O)C1=CC=CC=C1N>>CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([NH:16][c:17]2[c:18]([CH3:19])[n:20][n:21]([CH3:22])[c:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:1... | CONC(=O)c1ccccc1N.Cc1nn(C)c(C)c1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1ccccc1Nc1cc(Nc2c(C)nn(C)c2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 89.15 | [{"value": 89.15, "product": "CC1=C(C(=NN1C)C)NC2=NC=C(C(=C2)NC3=CC=CC=C3C(=O)NOC)C(F)(F)F", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-amino-N-methoxybenzamide (541 mg, 3.26 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (166 mg, 0.29 mmol), cesium carbonate (1249 mg, 3.83 mmol) and diacetoxypalladium (38.7 mg, 0.17 mmol) were added to a stirred solution of 4-iodo-5-(trifluoromethyl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)pyridin-2-ami... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1ccccc1N.Cc1nn(C)c(C)c1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccccc1Nc1cc(Nc2c(C)nn(C)c2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-971fd86c0ca2434fb005b5350f485988 | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][... | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4occc34)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 90.08 | [{"value": 90.08, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | 20/10 2009 10:10:14 +0200 To ethyl 4-bromobenzofuran-2-carboxylate (2.50 g, 9.29 mmol) and 1-benzylpiperazine (1.776 mL, 10.22 mmol) in dry degassed dioxane (30 mL) were added Cesium carbonate (3.94 g, 12.08 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.443 g, 0.93 mmol) and Tris(dibenzylideneacetone... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3a55abb970674d2a9a710b323cb93eee | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][... | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4occc34)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | **Purpose:** Buchwald-Hartwig coupling using unpurified ethyl 4-bromobenzofuran-2-carboxylate. The analysis on crude 4-bromobenzofuran-2-carboxylate shows traces of non cyclized and non aromoatized by-products. 2010-03-10 16:38:11: To a 25 mL rounbottomed flask was added ethyl 4-bromobenzofuran-2-carboxylate (1 g; 3.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c63ae2b686b74eaaae695094af43fe92 | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][... | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4occc34)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 26.58 | [{"value": 26.58, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | ethyl 4-bromobenzofuran-2-carboxylate (1 g, 3.72 mmol), 1-Benzylpiperazine (0.580 mL, 3.34 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.170 g, 0.19 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.177 g, 0.37 mmol) and CESIUM CARBONATE (1.574 g, 4.83 mmol) in dioxane (5 mL) were heated unde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-724091f002d04d2ea6bfe923f45ebf01 | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][... | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CC(C)(C)[O-].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4occc34)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 50 | CELSIUS | null | null | **Purpose:** Buchwald-Hartwig coupling using unpurified ethyl 4-bromobenzofuran-2-carboxylate. The analysis on crude 4-bromobenzofuran-2-carboxylate shows traces of non cyclized and non aromoatized by-products. 2010-03-02 15:25:22: To a 25 mL roundbottomed flask was added ethyl 4-bromobenzofuran-2-carboxylate (LR; 1 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2occc2c1 | HBr | CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 50 | null | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CCOC(=O)c1cc2c(N3C... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c0ea6369f2d042108e16225bf99070cf | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | CCOC(=O)C1=CC2=C(O1)C=CC=C2Br.C1CN(CCN1)CC2=CC=CC=C2>>CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4 | Br[c:9]1[c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[o:27][c:26]2[cH:25][cH:24][cH:23]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][... | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1 | CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 7a4de3d11f39bd07e4720041696f050c10dd028103577070ffc54089c7df5360 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cccc4occc34)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#8;a:6]:[c:5]2:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-3):[c:12]:2:[c:11]:1 | 31.9 | [{"value": 31.9, "product": "CCOC(=O)C1=CC2=C(C=CC=C2O1)N3CCN(CC3)CC4=CC=CC=C4", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | ethyl 4-bromobenzofuran-2-carboxylate (5 g, 18.58 mmol), 1-benzylpiperazine (3.22 mL, 18.58 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso- propyl-1,1'-biphenyl (0.886 g, 1.86 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.851 g, 0.93 mmol) and CESIUM CARBONATE (7.87 g, 24.16 mmol) were heated under argon to 95 °C... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2occc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 95 | null | CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-00b95f6f20354bb6923efd18c2b3c116 | Brc1ccccn1.C1CC2(CCN1)OCCO2>>c1ccc(N2CCC3(CC2)OCCO3)nc1 | C1=CC=NC(=C1)Br.C1CNCCC12OCCO2>>C1CN(CCC12OCCO2)C3=CC=CC=N3 | Br[c:4]1[cH:3][cH:2][cH:1][cH:16][n:15]1.[NH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[O:11][CH2:12][CH2:13][O:14]2>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][C:8]3([CH2:9][CH2:10]2)[O:11][CH2:12][CH2:13][O:14]3)[n:15][cH:16]1 | Brc1ccccn1.C1CC2(CCN1)OCCO2 | c1ccc(N2CCC3(CC2)OCCO3)nc1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 98501ed119dbc1fd4801d293f69e3d6501dd1371a251bfd1836b1cb54df9f3d3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCC3(CC2)OCCO3)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 66.56 | [{"value": 66.56, "product": "C1CN(CCC12OCCO2)C3=CC=CC=N3", "details": "", "is_desired": true}] | null | CELSIUS | null | null | The same procrdure as EN03653-93-01. | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1.C1CC2(CCN1)OCCO2 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | c1ccncc1.C1CC2(CC[NH]1)OCCO2 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd] | null | null | Brc1ccccn1.C1CC2(CCN1)OCCO2>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.CC(=O)O.CC(=O)O.[Pd]>c1ccc(N2CCC3(CC2)OCCO3)nc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-07751cbdbcad4c89bdfeeea3a04ddb39 | Clc1ccnc(Cl)n1.Nc1cccc(S(N)(=O)=O)c1>>NS(=O)(=O)c1cccc(Nc2nccc(Cl)n2)c1 | C1=CN=C(N=C1Cl)Cl.C1=CC(=CC(=C1)S(=O)(=O)N)N>>C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=CC(=N2)Cl | Cl[c:11]1[n:12][cH:13][cH:14][c:15]([Cl:16])[n:17]1.[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:18]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][cH:14][c:15]([Cl:16])[n:17]2)[cH:18]1 | Clc1ccnc(Cl)n1.Nc1cccc(S(N)(=O)=O)c1 | NS(=O)(=O)c1cccc(Nc2nccc(Cl)n2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 2 | [{"value": 2.0, "product": "C1=CC(=CC(=C1)S(=O)(=O)N)NC2=NC=CC(=N2)Cl", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | 2,4-dichloropyrimidine (200 mg, 1.34 mmol), 3-aminobenzenesulfonamide (231 mg, 1.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (93 mg, 0.16 mmol), cesium carbonate (875 mg, 2.68 mmol) and diacetoxypalladium (15.07 mg, 0.07 mmol) were suspended in dioxane (5 mL) and sealed into a microwave tube. Th... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | Clc1ccnc(Cl)n1.Nc1cccc(S(N)(=O)=O)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>NS(=O)(=O)c1cccc(Nc2nccc(Cl)n2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-2f71fc02b38b41c2a59bfdd4b865c8b3 | C1COCCN1.CCOC(=O)c1cncc(Br)c1>>CCOC(=O)c1cncc(N2CCOCC2)c1 | CCOC(=O)C1=CC(=CN=C1)Br.C1COCCN1>>CCOC(=O)C1=CC(=CN=C1)N2CCOCC2 | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Br[c:10]1[cH:9][n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17]1 | C1COCCN1.CCOC(=O)c1cncc(Br)c1 | CCOC(=O)c1cncc(N2CCOCC2)c1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:9]:[#7;a:8]:[c:7]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CC(=CN=C1)N2CCOCC2", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | ethyl 5-bromonicotinate (200 mg, 0.87 mmol), morpholine (0.083 mL, 0.96 mmol), sodium 2-methylpropan-2-olate (167 mg, 1.74 mmol), 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (17.11 mg, 0.04 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (19.90 mg, 0.02 mmol) were suspended in dioxane (5 mL) and sealed i... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 100 | null | C1COCCN1.CCOC(=O)c1cncc(Br)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bddc6734b7ce4143a8ed8f8385933b6e | C1COCCN1.CCOC(=O)c1cncc(Br)c1>>CCOC(=O)c1cncc(N2CCOCC2)c1 | CCOC(=O)C1=CC(=CN=C1)Br.C1COCCN1>>CCOC(=O)C1=CC(=CN=C1)N2CCOCC2 | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Br[c:10]1[cH:9][n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[cH:17]1 | C1COCCN1.CCOC(=O)c1cncc(Br)c1 | CCOC(=O)c1cncc(N2CCOCC2)c1 | CC(C)(C)[O-].[Na+] | CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:9]:[#7;a:8]:[c:7]:1 | 0 | [{"value": 0.0, "product": "CCOC(=O)C1=CC(=CN=C1)N2CCOCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | ethyl 5-bromonicotinate (200 mg, 0.87 mmol), morpholine (0.083 mL, 0.96 mmol), sodium 2-methylpropan-2-olate (167 mg, 1.74 mmol) and 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (17.11 mg, 0.04 mmol) were suspended in dioxane (5 mL). The reaction flask was purged with nitrogen and TRIS(DIBENZYLIDENEACETONE)D... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 80 | null | C1COCCN1.CCOC(=O)c1cncc(Br)c1>CC(C)(C)[O-].[Na+].CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>CCOC(=O)c1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-89890e81ad5d4e12a61d2ee591f39e46 | C1COCCN1.CC(C)(C)OC(=O)c1cncc(Br)c1>>CC(C)(C)OC(=O)c1cncc(N2CCOCC2)c1 | CC(C)(C)OC(=O)C1=CC(=CN=C1)Br.C1COCCN1>>CC(C)(C)OC(=O)C1=CC(=CN=C1)N2CCOCC2 | [NH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.Br[c:12]1[cH:11][n:10][cH:9][c:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][n:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19]1 | C1COCCN1.CC(C)(C)OC(=O)c1cncc(Br)c1 | CC(C)(C)OC(=O)c1cncc(N2CCOCC2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5902acad07b49263a420315db1dbdaba0aaad6beb97683ad32bdf77e8a68583b | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncc(N2CCOCC2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[c:9]:[c;H0;D3;+0:1](-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:2]:[#7;a:3]:[c:4]:1 | 26.56 | [{"value": 26.56, "product": "CC(C)(C)OC(=O)C1=CC(=CN=C1)N2CCOCC2", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | tert-butyl 5-bromonicotinate (1.4 g, 5.42 mmol), morpholine (0.591 ml, 6.78 mmol), cesium carbonate (3.53 g, 10.85 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.507 g, 0.81 mmol) were dissolved in toluene (20 ml). The reaction flask was purged with nitrogen and diacetoxypalladium (0.061 g, 0.27 mmol) was add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccncc1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | C1COCCN1.CC(C)(C)OC(=O)c1cncc(Br)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)c1cncc(N2CCOCC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-870573203c2744a5906bd6a9d998822e | Brc1ccc2cn[nH]c2c1.Nc1ccccc1Cl>>Clc1ccccc1Nc1ccc2cn[nH]c2c1 | C1=CC2=C(C=C1Br)NN=C2.C1=CC=C(C(=C1)N)Cl>>C1=CC=C(C(=C1)NC2=CC3=C(C=C2)C=NN3)Cl | Br[c:9]1[cH:10][cH:11][c:12]2[cH:13][n:14][nH:15][c:16]2[cH:17]1.[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH2:8]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[NH:8][c:9]1[cH:10][cH:11][c:12]2[cH:13][n:14][nH:15][c:16]2[cH:17]1 | Brc1ccc2cn[nH]c2c1.Nc1ccccc1Cl | Clc1ccccc1Nc1ccc2cn[nH]c2c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | ea97cdf2c8c980f6ebe24875f6c8aa55ce683b58ce5d3e4faa81fadc6d8e560f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3cn[nH]c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2:[c:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:2:[c:9]:1):[c:13] | 0 | [{"value": 0.0, "product": "C1=CC=C(C(=C1)NC2=CC3=C(C=C2)C=NN3)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium(II) acetate (0.342 g, 1.52 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.422 g, 2.28 mmol) were added to a stirred slurry of 2-chloroaniline (1.763 mL, 16.75 mmol), 6-bromo-1H-indazole (3 g, 15.23 mmol) and cesium carbonate (9.92 g, 30.45 mmol) in toluene (50 mL) at 23°C under nitrogen. The res... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccccc1.c1ccc2n[nH]cc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | Brc1ccc2cn[nH]c2c1.Nc1ccccc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>Clc1ccccc1Nc1ccc2cn[nH]c2c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e759108cf109420c9b96a1936ea5e56d | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CC=CC=C5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:1... | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 37.23 | [{"value": 37.23, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5=CC=CC=C5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (60.0 mg, 0.22 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (57.7 mg, 0.28 mmol), palladium(II) acetate (4.90 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (7.65 mg, 0.02 mmol) and CS2CO3 (213 mg, 0.66 mmol) were weighed into a microw... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8e16338c39aa405d9e6607bfaa8d820e | CN1CCNCC1.Oc1ccc(Br)cc1>>CN1CCN(c2ccc(O)cc2)CC1 | C1=CC(=CC=C1O)Br.CN1CCNCC1>>CN1CCN(CC1)C2=CC=C(C=C2)O | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1.Br[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]2)[CH2:13][CH2:14]1 | CN1CCNCC1.Oc1ccc(Br)cc1 | CN1CCN(c2ccc(O)cc2)CC1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 50.99 | [{"value": 50.99, "product": "CN1CCN(CC1)C2=CC=C(C=C2)O", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | diacetoxypalladium (0.039 g, 0.17 mmol) was added in one portion to 4-bromophenol (3 g, 17.34 mmol) and 1-methylpiperazine (2.308 mL, 20.81 mmol) in toluene (87 mL) at 25°C under nitrogen. To this was added toluene (87 mL) then a solution of 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.123 mL, ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | CN1CCNCC1.Oc1ccc(Br)cc1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>CN1CCN(c2ccc(O)cc2)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-e129276e5a184223a5b0f70438a49a49 | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C1OC2=C(C(=CN=C2O1)Cl)N.C1CC1C(=O)NC2=NC=CC(=C2)Cl>>C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][n:12][c:13]2[c:14]1[O:15][CH2:16][O:17]2.Cl[c:6]1[cH:5][c:4]([NH:3][C:2](=[O:1])[CH:21]2[CH2:22][CH2:23]2)[n:20][cH:19][cH:18]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([NH:7][c:8]2[c:9]([Cl:10])[cH:11][n:12][c:13]3[c:14]2[O:15][CH2:16][O:17]3)[cH:18][cH:19][n:20]1)[CH:21]1[CH2:22][CH2:23... | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1 | O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(Nc1cc(Nc2ccnc3c2OCO3)ccn1)C1CC1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1.[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH2;D1;+0:17]>>[#8:10]-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[c:15]:[c:16]:1-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]-[C:7]=[O;D1;H0:8]):[c:9]:1 | 59.09 | [{"value": 59.09, "product": "C1CC1C(=O)NC2=NC=CC(=C2)NC3=C4C(=NC=C3Cl)OCO4", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | To a stirred solution of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (15 g, 76.28 mmol) in dioxane (200 mL) was added 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (13.16 g, 76.28 mmol), cesium carbonate (62.1 g, 190.71 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.86 g, 8.39 mmol) and diacetoxy... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cnc2c(c1)OCO2.C1CC1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 110 | null | Nc1c(Cl)cnc2c1OCO2.O=C(Nc1cc(Cl)ccn1)C1CC1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-59e34daf62ce45d3ab308432983c78e6 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>>O=C1NCCc2cc(NCc3ccccc3)ccc21 | C1CNC(=O)C2=C1C=C(C=C2)Br.C1=CC=C(C=C1)CN>>C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3 | [NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[c:8]1[cH:7][c:6]2[c:19]([cH:18][cH:17]1)[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]21 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21 | O=C1NCCc2cc(NCc3ccccc3)ccc21 | CC(C)(C)[O-].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d7705807f28ffea93f48a808a972820efea4f0d0bf760da3f3ded46d188f54b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cc(NCc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | In a 5 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (6.89 mg, 0.01 mmol) and palladium(II) acetate (2.483 mg, 0.01 mmol) in DMF (500 mL) combined to give a tan suspension. potassium tert-butoxide (24.82 mg, 0.22 mmol) was then added... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O | 130 | null | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O>O=C1NCCc2cc(NCc3ccccc3)ccc21 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-08bf18171af14ad9bb3d94faf7cd7b73 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>>O=C1NCCc2cc(NCc3ccccc3)ccc21 | C1CNC(=O)C2=C1C=C(C=C2)Br.C1=CC=C(C=C1)CN>>C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3 | [NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[c:8]1[cH:7][c:6]2[c:19]([cH:18][cH:17]1)[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]21 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21 | O=C1NCCc2cc(NCc3ccccc3)ccc21 | C[O-].[Na+] | C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d7705807f28ffea93f48a808a972820efea4f0d0bf760da3f3ded46d188f54b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cc(NCc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a small MW* sealed test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (24.16 µl, 0.22 mmol), palladium(II) acetate (2.483 mg, 0.01 mmol), Ethylenebis(diphenylphosphine) (8.81 mg, 0.02 mmol) and sodium methoxide (13.14 mg, 0.24 mmol) in toluene (2188 µl) combined to give a or... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccccc1 | HBr | C[O-].[Na+].C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 110 | null | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>C[O-].[Na+].C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>O=C1NCCc2cc(NCc3ccccc3)ccc21 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-77ff9a88bff94b57b6f8498de8922bdf | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>>O=C1NCCc2cc(NCc3ccccc3)ccc21 | C1CNC(=O)C2=C1C=C(C=C2)Br.C1=CC=C(C=C1)CN>>C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3 | [NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[c:8]1[cH:7][c:6]2[c:19]([cH:18][cH:17]1)[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]21 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21 | O=C1NCCc2cc(NCc3ccccc3)ccc21 | CC(C)(C)[O-].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d7705807f28ffea93f48a808a972820efea4f0d0bf760da3f3ded46d188f54b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cc(NCc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | **Repeat 02915-84 but use MW* only. Reduce benzylamine from 4 to 2 eqs.** In a 10 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.44 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (13.77 mg, 0.02 mmol) and palladium(II) acetate (4.97 mg, 0.02 mmol) in DMF (500 mL) combined to give ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O | 130 | null | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O>O=C1NCCc2cc(NCc3ccccc3)ccc21 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-4a6bd61cd0ff477baa0ad5e567d741e9 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>>O=C1NCCc2cc(NCc3ccccc3)ccc21 | C1CNC(=O)C2=C1C=C(C=C2)Br.C1=CC=C(C=C1)CN>>C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3 | [NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.Br[c:8]1[cH:7][c:6]2[c:19]([cH:18][cH:17]1)[C:2](=[O:1])[NH:3][CH2:4][CH2:5]2>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[cH:7][c:8]([NH:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]21 | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21 | O=C1NCCc2cc(NCc3ccccc3)ccc21 | CC(C)(C)[O-].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d7705807f28ffea93f48a808a972820efea4f0d0bf760da3f3ded46d188f54b2 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1NCCc2cc(NCc3ccccc3)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "C1CNC(=O)C2=C1C=C(C=C2)NCC3=CC=CC=C3", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | **Repeat 02915-84 but use NO solvent** In a 5 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (6.89 mg, 0.01 mmol) and palladium(II) acetate (2.483 mg, 0.01 mmol) combined to give a tan suspension. potassium tert-butoxide (24.82 mg, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccccc1 | HBr | CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | 130 | null | NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd]>O=C1NCCc2cc(NCc3ccccc3)ccc21 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-1de120ae65d949b5bd42bbdc8c6567d2 | CC(=O)N1Cc2ccc(Cl)nc2OC(COC(C)C)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 | CC(C)OCC1CN(CC2=C(O1)N=C(C=C2)Cl)C(=O)C.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C(=O)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH2:15][O:16][CH:17]([CH3:18])[CH3:19])[CH2:20][N:21]([C:22]([CH3:23])=[O:24])[CH2:25]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:26][cH:27][c:28]1-[n:29]1[cH:30][n:31][c:32]([CH3:33])[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([... | CC(=O)N1Cc2ccc(Cl)nc2OC(COC(C)C)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OCCNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 14.66 | [{"value": 14.66, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)COC(C)C)C(=O)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 1-(8-chloro-2-(isopropoxymethyl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone (0.169 g, 0.57 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.115 g, 0.57 mmol), Palladium acetate (0.013 g, 0.06 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.020 g, 0.06 mmol) and Cesium carbonate (0.553 g, 1.70 mmol) wer... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CC(=O)N1Cc2ccc(Cl)nc2OC(COC(C)C)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(COC(C)C)CN(C(C)=O)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-31c66ec343f04bfcb7e9caaf0de27de4 | N#Cc1ccc(Br)cc1F.Nc1ccccc1Cl>>N#Cc1ccc(Nc2ccccc2Cl)cc1F | C1=CC(=C(C=C1Br)F)C#N.C1=CC=C(C(=C1)N)Cl>>C1=CC=C(C(=C1)NC2=CC(=C(C=C2)C#N)F)Cl | Br[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:16]([F:17])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[Cl:14])[cH:15][c:16]1[F:17] | N#Cc1ccc(Br)cc1F.Nc1ccccc1Cl | N#Cc1ccc(Nc2ccccc2Cl)cc1F | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 83.52 | [{"value": 83.52, "product": "C1=CC=C(C(=C1)NC2=CC(=C(C=C2)C#N)F)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | Palladium(II) acetate (0.561 g, 2.50 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (2.335 g, 3.75 mmol) was added to a stirred slurry of 2-chloroaniline (2.63 mL, 25.00 mmol), 4-bromo-2-fluorobenzonitrile (5 g, 25.00 mmol) and cesium carbonate (16.29 g, 50.00 mmol) in toluene (180 mL) at 23°Cunder nitrogen.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 80 | null | N#Cc1ccc(Br)cc1F.Nc1ccccc1Cl>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>N#Cc1ccc(Nc2ccccc2Cl)cc1F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-019ad9f92b5c40ecbf5416e8a6461063 | COc1cc2c(cc1N)N(C(C)=O)CC2.Cc1cnc(Cl)nc1-c1cnn2ccccc12>>COc1cc2c(cc1Nc1ncc(C)c(-c3cnn4ccccc34)n1)N(C(C)=O)CC2 | CC1=CN=C(N=C1C2=C3C=CC=CN3N=C2)Cl.CC(=O)N1CCC2=CC(=C(C=C21)N)OC>>CC1=CN=C(N=C1C2=C3C=CC=CN3N=C2)NC4=C(C=C5CCN(C5=C4)C(=O)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH2:9])[N:26]([C:27]([CH3:28])=[O:29])[CH2:30][CH2:31]2.Cl[c:10]1[n:11][cH:12][c:13]([CH3:14])[c:15](-[c:16]2[cH:17][n:18][n:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH:9][c:10]1[n:11][cH:12][c:13]([CH3:14])[c:15]... | COc1cc2c(cc1N)N(C(C)=O)CC2.Cc1cnc(Cl)nc1-c1cnn2ccccc12 | COc1cc2c(cc1Nc1ncc(C)c(-c3cnn4ccccc34)n1)N(C(C)=O)CC2 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccn2ncc(-c3ccnc(Nc4ccc5c(c4)NCC5)n3)c2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 46.76 | [{"value": 46.76, "product": "CC1=CN=C(N=C1C2=C3C=CC=CN3N=C2)NC4=C(C=C5CCN(C5=C4)C(=O)C)OC", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | A mixture of 3-(2-chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine (400 mg, 1.55 mmol), 1-(6-amino-5-methoxyindolin-1-yl)ethanone (341 mg, 1.55 mmol) and diacetoxypalladium (34.9 mg, 0.16 mmol) 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (97 mg, 0.16 mmol) cesium carbonate (759 mg, 2.33 mmol) were degassed with ni... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccn2nccc2c1.c1ccc2c(c1)CC[NH]2 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | COc1cc2c(cc1N)N(C(C)=O)CC2.Cc1cnc(Cl)nc1-c1cnn2ccccc12>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc2c(cc1Nc1ncc(C)c(-c3cnn4ccccc34)n1)N(C(C)=O)CC2 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0ff30e2abe284325a98db1564fc934f7 | COc1cc(N)ccc1-n1cnc(C)c1.Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1>>COc1cc(Nc2ccc3c(n2)OC(c2cc(C)nn2C)CN(CC#N)C3)ccc1-n1cnc(C)c1 | CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)CC#N)C.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=CC(=C(C=C4)N5C=C(N=C5)C)OC)CC#N)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:28][cH:29][c:30]1-[n:31]1[cH:32][n:33][c:34]([CH3:35])[cH:36]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([c:15]1[cH:16][c:17]([CH3:18])[n:19][n:20]1[CH3:21])[CH2:22][N:23]([CH2:24][C:25]#[N:26])[CH2:27]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10... | COc1cc(N)ccc1-n1cnc(C)c1.Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1 | COc1cc(Nc2ccc3c(n2)OC(c2cc(C)nn2C)CN(CC#N)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(c3ccn[nH]3)CNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 16.55 | [{"value": 16.55, "product": "CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=CC(=C(C=C4)N5C=C(N=C5)C)OC)CC#N)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.068 g, 0.34 mmol),2-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (0.107 g, 0.34 mmol) Palladium acetate (7.56 mg, 0.03 mmol) and Cesium carbonate (0.329 g, 1.01 mmol) were added in a microwave vial. The mixture ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1cc[nH]n1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1-n1cnc(C)c1.Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(c2cc(C)nn2C)CN(CC#N)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-879180a104c8430c87fe873fe28d1e66 | CONC(=O)c1cc(F)ccc1N.FC(F)(F)c1cnc(Cl)cc1I>>CONC(=O)c1cc(F)ccc1Nc1cc(Cl)ncc1C(F)(F)F | C1=C(C(=CN=C1Cl)C(F)(F)F)I.CONC(=O)C1=C(C=CC(=C1)F)N>>CONC(=O)C1=C(C=CC(=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[C:21]([F:22])([F:23])[F:24]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[C:21]([F:22])([F:23])[... | CONC(=O)c1cc(F)ccc1N.FC(F)(F)c1cnc(Cl)cc1I | CONC(=O)c1cc(F)ccc1Nc1cc(Cl)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;... | 40.43 | [{"value": 40.43, "product": "CONC(=O)C1=C(C=CC(=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (0.502 g, 1.63 mmol), 2-amino-5-fluoro-N-methoxybenzamide (0.344 g, 1.68 mmol), diacetoxypalladium (0.029 g, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.151 g, 0.26 mmol) and cesium carbonate (0.638 g, 1.96 mmol) were weighed out in a microwave vi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1cc(F)ccc1N.FC(F)(F)c1cnc(Cl)cc1I>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1cc(F)ccc1Nc1cc(Cl)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-314790a0639b418890793562fb7875b5 | CONC(=O)c1ccc(F)cc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1ccc(F)cc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=C(C=C(C=C1)F)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([NH:17][c:18]2[cH:19][n:20]([CH3:21])[n:22][c:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16](... | CONC(=O)c1ccc(F)cc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1ccc(F)cc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 39.62 | [{"value": 39.62, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (24.98 mg, 0.04 mmol), diacetoxypalladium (5.82 mg, 0.03 mmol), 2-amino-4-fluoro-N- methoxybenzamide (90 mg, 0.49 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (110 mg, 0.29 mmol) and cesium carbonate (188 mg, 0.58 mmol) were ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 95 | null | CONC(=O)c1ccc(F)cc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1ccc(F)cc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-64de42ce56244836b512746d4c6a3fee | COc1cc(N)ccc1-n1cnc(C)c1.N#CCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CC#N)C3)ccc1-n1cnc(C)c1 | C1[C@H](OC2=C(CN1CC#N)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)CC#N)C=C3)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][cH:28][c:29]1-[n:30]1[cH:31][n:32][c:33]([CH3:34])[cH:35]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH2:23][C:24]#[N:25])[CH2:26]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11... | COc1cc(N)ccc1-n1cnc(C)c1.N#CCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1 | COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CC#N)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 7.81 | [{"value": 7.81, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)CC#N)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (195 mg, 0.96 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (288 mg, 0.96 mmol) Palladium acetate (21.55 mg, 0.10 mmol) and Cesium carbonate (938 mg, 2.88 mmol) were added in a microwave vial. The mixture was capped and flushe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1-n1cnc(C)c1.N#CCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CC#N)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d3bf2a42ca064635a16f6a54a057bf59 | COc1cc(N)ccc1-n1cnc(C)n1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1-n1cnc(C)n1 | C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3.CC1=NN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)CCO)C=C3)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][cH:28][c:29]1-[n:30]1[cH:31][n:32][c:33]([CH3:34])[n:35]1.Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH2:23][CH2:24][OH:25])[CH2:26]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:1... | COc1cc(N)ccc1-n1cnc(C)n1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1 | COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1-n1cnc(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 21.28 | [{"value": 21.28, "product": "CC1=NN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)CCO)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (67.0 mg, 0.33 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (100 mg, 0.33 mmol), Palladium acetate (7.37 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (11.50 mg, 0.03 mmol) and Cesium carbonate (321 mg, 0.98 mmol) were add... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1nc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1-n1cnc(C)n1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1-n1cnc(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-20ba80f324544fc48cbce515702585f3 | COc1cc(N)ccc1-n1cnc(C)c1.Clc1ncccn1>>COc1cc(Nc2ncccn2)ccc1-n1cnc(C)c1 | C1=CN=C(N=C1)Cl.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=CC=N3)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:13][cH:14][c:15]1-[n:16]1[cH:17][n:18][c:19]([CH3:20])[cH:21]1.Cl[c:7]1[n:8][cH:9][cH:10][cH:11][n:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][cH:10][cH:11][n:12]2)[cH:13][cH:14][c:15]1-[n:16]1[cH:17][n:18][c:19]([CH3:20])[cH:21]1 | COc1cc(N)ccc1-n1cnc(C)c1.Clc1ncccn1 | COc1cc(Nc2ncccn2)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc(Nc2ccc(-n3ccnc3)cc2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 18.78 | [{"value": 18.78, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=CC=N3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-Chloropyrimidine (0.056 g, 0.49 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.100 g, 0.49 mmol), Palladium acetate (0.011 g, 0.05 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.017 g, 0.05 mmol) and Cesium carbonate (0.481 g, 1.48 mmol) were placed in a microwave vial. The mixture was capped and flushed with... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1-n1cnc(C)c1.Clc1ncccn1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ncccn2)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-eb19acfe7f704eb2aa769ff5f1767708 | CNc1ccc(F)cc1.OCc1ccnc(Cl)c1>>CN(c1ccc(F)cc1)c1cc(CO)ccn1 | C1=CN=C(C=C1CO)Cl.CNC1=CC=C(C=C1)F>>CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)CO | [CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1.Cl[c:10]1[cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16][n:17]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][c:12]([CH2:13][OH:14])[cH:15][cH:16][n:17]1 | CNc1ccc(F)cc1.OCc1ccnc(Cl)c1 | CN(c1ccc(F)cc1)c1cc(CO)ccn1 | CC(C)(C)[O-].[K+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)CO", "details": "", "is_desired": true}] | 105 | CELSIUS | null | null | In a 50 mL round-bottomed flask (t=g) was (2-chloropyridin-4-yl)methanol (.1 g, 0.70 mmol), Pd2dba3 (0.032 g, 0.03 mmol), and biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol) in toluene (6 mL) to give a dark red solution. 4-fluoro-N-methylaniline (0.096 g, 0.77 mmol) and KOtBu (.323 g, 2.88 mmol) were added. Mi... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HCl | CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 105 | null | CNc1ccc(F)cc1.OCc1ccnc(Cl)c1>CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN(c1ccc(F)cc1)c1cc(CO)ccn1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-d1bfb220e27441fcb5908d58a9e8690c | Brc1cncc(Br)c1.CNc1ccc(F)cc1>>CN(c1ccc(F)cc1)c1cncc(Br)c1 | C1=C(C=NC=C1Br)Br.CNC1=CC=C(C=C1)F>>CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br | Br[c:10]1[cH:11][n:12][cH:13][c:14]([Br:15])[cH:16]1.[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][n:12][cH:13][c:14]([Br:15])[cH:16]1 | Brc1cncc(Br)c1.CNc1ccc(F)cc1 | CN(c1ccc(F)cc1)c1cncc(Br)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 0 | [{"value": 0.0, "product": "CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a 50 mL round-bottomed flask (t=g) was 4-fluoro-N-methylaniline (.05 g, 0.40 mmol), 3,5-dibromopyridine (0.114 g, 0.48 mmol), and Pd2(dba)3 (0.018 g, 0.02 mmol) in toluene (16 mL) ([VOLUME]) to give a purple suspension. biphenyl-2-yldicyclohexylphosphine (0.021 g, 0.06 mmol) and CS2CO3 (0.195 g, 0.60 mmol) were adde... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | Brc1cncc(Br)c1.CNc1ccc(F)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN(c1ccc(F)cc1)c1cncc(Br)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-49953a76cfae45059ad30fb1a9e6e7be | Brc1cncc(Br)c1.CNc1ccc(F)cc1>>CN(c1ccc(F)cc1)c1cncc(Br)c1 | C1=C(C=NC=C1Br)Br.CNC1=CC=C(C=C1)F>>CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br | Br[c:10]1[cH:11][n:12][cH:13][c:14]([Br:15])[cH:16]1.[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][n:12][cH:13][c:14]([Br:15])[cH:16]1 | Brc1cncc(Br)c1.CNc1ccc(F)cc1 | CN(c1ccc(F)cc1)c1cncc(Br)c1 | CC(C)(C)[O-].[K+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C;D1;H3:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 12.46 | [{"value": 12.46, "product": "CN(C1=CC=C(C=C1)F)C2=CC(=CN=C2)Br", "details": "", "is_desired": true}] | 110 | CELSIUS | null | null | In a 50 mL round-bottomed flask (t=g) was 4-fluoro-N-methylaniline (1 g, 7.99 mmol), 3,5-dibromopyridine (2.272 g, 9.59 mmol), and Pd2(dba)3 (0.366 g, 0.40 mmol) in toluene (16 mL) ([VOLUME]) to give a purple suspension. biphenyl-2-yldicyclohexylphosphine (0.420 g, 1.20 mmol) and KOtBu (1.166 g, 10.39 mmol) were added.... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HBr | CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 110 | null | Brc1cncc(Br)c1.CNc1ccc(F)cc1>CC(C)(C)[O-].[K+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CN(c1ccc(F)cc1)c1cncc(Br)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a109f4c2b76742478a5e890f91f99d62 | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | CS(=O)(=O)C1=CC=C(C=C1)Br.C1=C(N=C(C=N1)Cl)N>>CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl | Br[c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:18][cH:17]1.[NH2:9][c:10]1[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]2)[cH:17][cH:18]1 | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1 | CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:4]:[c:5] | 70.51 | [{"value": 70.51, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | _1-bromo-4-(methylsulfonyl)benzene (1410 mg, 6.00 mmol)_ _then_ _cesium carbonate (2540 mg, 7.80 mmol)_ _ were successively added to a solution of __6-chloropyrazin-2-amine (777 mg, 6.00 mmol)_ _ _ _1,4-dioxane (20 ml)_ _into a microwave reactor._ _The mixture was purged by bubbling nitrogen for 5 minutes, then_ ___(9... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnccn1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fb9234fb5e36477680c49d193f20e84f | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | CS(=O)(=O)C1=CC=C(C=C1)Br.C1=C(N=C(C=N1)Cl)N>>CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl | Br[c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:18][cH:17]1.[NH2:9][c:10]1[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]2)[cH:17][cH:18]1 | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1 | CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1):[c:4]:[c:5] | 89.91 | [{"value": 89.91, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | _1-bromo-4-(methylsulfonyl)benzene (4.70 g, 19.99 mmol)_ _then_ _cesium carbonate (8.47 g, 25.99 mmol)_ _ were successively added to a solution of __6-chloropyrazin-2-amine (2.59 g, 19.99 mmol)_ _ _ _1,4-dioxane (75 ml)_ _into a microwave reactor._ _The mixture was purged by bubbling nitrogen for 5 minutes, then_ ___(... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnccn1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CS(=O)(=O)c1ccc(Br)cc1.Nc1cncc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ea53d8feb8094f94b89810756f770f19 | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1ccc(Br)cc1)C12CCC(CC1)N2C>>Cc1cccc(C)c1C(=O)NC(c1ccc(N2CCOCC2)cc1)C12CCC(CC1)N2C | CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC=C(C=C2)Br)C34CCC(N3C)CC4.C1COCCN1>>CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC=C(C=C2)N3CCOCC3)C45CCC(N4C)CC5 | [NH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1.Br[c:16]1[cH:15][cH:14][c:13]([CH:12]([NH:11][C:9]([c:8]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]2[CH3:7])=[O:10])[C:25]23[CH2:26][CH2:27][CH:28]([CH2:29][CH2:30]2)[N:31]3[CH3:32])[cH:24][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1[C:9](=[O:10])[NH:11][CH:12... | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1ccc(Br)cc1)C12CCC(CC1)N2C | Cc1cccc(C)c1C(=O)NC(c1ccc(N2CCOCC2)cc1)C12CCC(CC1)N2C | CC(C)(C)[O-].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(NC(c1ccc(N2CCOCC2)cc1)C12CCC(CC1)N2)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 29.57 | [{"value": 29.57, "product": "CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC=C(C=C2)N3CCOCC3)C45CCC(N4C)CC5", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | In a CEM microwave vial was N-((4-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (100 mg, 0.23 mmol), morpholine (0.082 mL, 0.94 mmol), palladium(II) acetate (5.25 mg, 0.02 mmol), BINAP (14.57 mg, 0.02 mmol), and potassium tert-butoxide (52.5 mg, 0.47 mmol) solid and DMF (2 mL) was a... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | C1CC2CCC1[NH]2.c1ccccc1.c1ccccc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O | 130 | null | C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1ccc(Br)cc1)C12CCC(CC1)N2C>CC(C)(C)[O-].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CN(C)C=O>Cc1cccc(C)c1C(=O)NC(c1ccc(N2CCOCC2)cc1)C12CCC(CC1)N2C |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9ef98b7f45644360a694676cf7d7ef09 | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH:15]1[CH2:16][CH2:17]1)[CH2:18][N:19]([CH3:20])[CH2:21]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:22][cH:23][c:24]1-[n:25]1[cH:26][n:27][c:28]([CH3:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]([CH:15]2... | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(C3CC3)CNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.249 g, 1.22 mmol), 8-chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.292 g, 1.22 mmol), Palladium acetate (0.027 g, 0.12 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.043 g, 0.12 mmol) and Cesium carbonate (0.399 g, 1.22 mmol) were added in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.C1CC1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8b7a42439bc84286a389b0a321434e15 | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH:15]1[CH2:16][CH2:17]1)[CH2:18][N:19]([CH3:20])[CH2:21]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:22][cH:23][c:24]1-[n:25]1[cH:26][n:27][c:28]([CH3:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]([CH:15]2... | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(C3CC3)CNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.031 g, 0.15 mmol), 8-chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.036 g, 0.15 mmol), Palladium acetate (3.39 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (5.29 mg, 0.02 mmol) and Cesium carbonate (0.049 g, 0.15 mmol) were added in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.C1CC1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-9e945d87965540af8be94a72eefc3798 | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1CC(OC2=C(C1)C=CC(=N2)Cl)C3CC3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC | Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][CH:14]([CH:15]1[CH2:16][CH2:17]1)[CH2:18][N:19]([CH3:20])[CH2:21]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:22][cH:23][c:24]1-[n:25]1[cH:26][n:27][c:28]([CH3:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][CH:14]([CH:15]2... | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(C3CC3)CNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(CC(O4)C5CC5)C)C=C3)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.189 g, 0.93 mmol), 8-chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.222 g, 0.93 mmol), Palladium acetate (0.021 g, 0.09 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.033 g, 0.09 mmol) and Cesium carbonate (0.303 g, 0.93 mmol) were added in ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.C1CC1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2ccc(Cl)nc2OC(C2CC2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)OC(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7d01f29fd6fc44f08392db2774553827 | COc1cc(N)ccc1C#N.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1C#N | C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3.COC1=C(C=CC(=C1)N)C#N>>COC1=C(C=CC(=C1)NC2=NC3=C(CN(C[C@H](O3)C4=CC=CC=C4)CCO)C=C2)C#N | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][cH:28][c:29]1[C:30]#[N:31].Cl[c:7]1[cH:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH2:23][CH2:24][OH:25])[CH2:26]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]3[c:11]([n:12]2)[O:13][C@H:14]([c:15... | COc1cc(N)ccc1C#N.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1 | COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1C#N | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CNC3)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 13.17 | [{"value": 13.17, "product": "COC1=C(C=CC(=C1)NC2=NC3=C(CN(C[C@H](O3)C4=CC=CC=C4)CCO)C=C2)C#N", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-amino-2-methoxybenzonitrile (72.9 mg, 0.49 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (150 mg, 0.49 mmol), Palladium acetate (11.05 mg, 0.05 mmol), 2-(Dicyclohexylphosphino)biphenyl (17.25 mg, 0.05 mmol)and Cesium carbonate (481 mg, 1.48 mmol) were added to a microwave via... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccccc1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1C#N.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(CCO)C3)ccc1C#N |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b814b75406f3451f844066ae5ac468ab | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[K+].[K+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | Purpose: to examine scale-up of microwave conditions established in a previous experiment. Charged a round-bottom flask with a mixture of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.702 g, 3.45 mmol), (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (1.0 g, 3.63 mmol), palladium (II... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[K+].[K+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3d675e76027a44c193655dafbce49365 | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 15 | [{"value": 15.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (0.05 g, 0.18 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.037 g, 0.18 mmol) (0.65), PALLADIUM(II) ACETATE (1.221 mg, 5.44 µmol), CESIUM CARBONATE (0.071 g, 0.22 mmol) and Tri-tert- butylphosphonium tetrafluoriborate (0.0043 g, 0... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-3a2eb97137e148aba58c08979aa7d29e | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CCC(C)(C)[O-].[Na+] | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (0.05 g, 0.18 mmol), PALLADIUM(II) ACETATE (1.221 mg, 5.44 µmol) (1.6), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.037 g, 0.18 mmol) (0.64), Tri-tert- butylphosphonium tetrafluoriborate (0.0043 g, 0.014 mmol, 6 mol%) and Na-t-amilate ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | CCC(C)(C)[O-].[Na+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 120 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>CCC(C)(C)[O-].[Na+].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-8ae4472e49574adcac504920ccdd2d20 | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 30.38 | [{"value": 30.38, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (400 mg, 1.45 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (265 mg, 1.31 mmol), Cesium carbonate (709 mg, 2.18 mmol), Palladium(II) acetate (32.6 mg, 0.15 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (168 mg, 0.29 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 130 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-53ad2bbc851349aeae5fd4d95fae57a4 | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 120 | CELSIUS | null | null | The aim is optimization. (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (29 mg, 0.11 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (21.38 mg, 0.11 mmol), Sodium tert-butoxide (15.16 mg, 0.16 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (9.17 mg, 0.01 mmol) and Tris(dib... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 120 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5df7b290b65549a1949a950ac953d2d5 | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 6.84 | [{"value": 6.84, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Palladium(II) acetate (6.68 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (10.42 mg, 0.03 mmol) and Cesium carbonate (0.388 g, 1.19 mmol) were put in a 5 mL microwave vial and sealed. The vial was flushed with argon. (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (0.082 g, 0.30 mmol)... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-71ed8e3015a64fa5b6ac3b0bc984c3fc | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | CN1C[C@H](OC2=NC(=NC=C2C1)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC | Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH3:23])[CH2:24]2.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[n:28]1[cH:29][n:30][c:31]([CH3:32])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]([n:12]2)[O:13... | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 0 | [{"value": 0.0, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)C)OC", "details": "", "is_desired": true}] | 130 | CELSIUS | null | null | The aim is optimization. (R)-2-chloro-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepine (30 mg, 0.11 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (22.11 mg, 0.11 mmol), Cesium carbonate (53.2 mg, 0.16 mmol), [Reactants] and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (12.59 mg, 0.02 mmol) ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1 | 130 | null | CN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1COCCO1>COc1cc(N... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5b8b8e8b9f444b0ba792e38397226bc2 | COc1cc(N)ccc1-n1cnc(C)c1.FCCN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1>>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(CCF)C3)ccc1-n1cnc(C)c1 | C1[C@H](OC2=NC(=NC=C2CN1CCF)Cl)C3=CC=CC=C3.CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC>>CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)CCF)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][cH:28][c:29]1-[n:30]1[cH:31][n:32][c:33]([CH3:34])[cH:35]1.Cl[c:7]1[n:8][cH:9][c:10]2[c:11]([n:12]1)[O:13][C@H:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][N:22]([CH2:23][CH2:24][F:25])[CH2:26]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[c:11]... | COc1cc(N)ccc1-n1cnc(C)c1.FCCN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1 | COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(CCF)C3)ccc1-n1cnc(C)c1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | e454e65c0d736a4462cb77fe7466aced962a67d7fcf862fdf6564bf1094d2902 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3cnc(Nc4ccc(-n5ccnc5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 14.93 | [{"value": 14.93, "product": "CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC=C4CN(C[C@H](OC4=N3)C5=CC=CC=C5)CCF)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.118 g, 0.49 mmol), Palladium(II) acetate (9.19 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.014 g, 0.04 mmol) and Cesium carbonate (0.00 µmol) were put in a 5 mL microwave vial and sealed and purged with argon. (R)-2-chloro-6-(2-fluoroethyl)-8-phenyl-5,6,7,8-tet... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)OCC[NH]C2 | c1ncc2c(n1)OCC[NH]C2 | c1ccccc1.c1ncc2c(n1)OCC[NH]C2.c1ccccc1.c1c[nH]cn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | COc1cc(N)ccc1-n1cnc(C)c1.FCCN1Cc2cnc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>COc1cc(Nc2ncc3c(n2)O[C@H](c2ccccc2)CN(CCF)C3)ccc1-n1cnc(C)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fe46b53c9b194686811f12ba6b3f2abb | Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1.Cc1nccn1-c1ccc(N)cc1>>Cc1cc(C2CN(CC#N)Cc3ccc(Nc4ccc(-n5ccnc5C)cc4)nc3O2)n(C)n1 | CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)Cl)CC#N)C.CC1=NC=CN1C2=CC=C(C=C2)N>>CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=CC=C(C=C4)N5C=CN=C5C)CC#N)C | Cl[c:15]1[cH:14][cH:13][c:12]2[c:30]([n:29]1)[O:31][CH:5]([c:4]1[cH:3][c:2]([CH3:1])[n:34][n:32]1[CH3:33])[CH2:6][N:7]([CH2:8][C:9]#[N:10])[CH2:11]2.[NH2:16][c:17]1[cH:18][cH:19][c:20](-[n:21]2[cH:22][cH:23][n:24][c:25]2[CH3:26])[cH:27][cH:28]1>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]2[CH2:6][N:7]([CH2:8][C:9]#[N:10])[CH2:11][... | Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1.Cc1nccn1-c1ccc(N)cc1 | Cc1cc(C2CN(CC#N)Cc3ccc(Nc4ccc(-n5ccnc5C)cc4)nc3O2)n(C)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn(-c2ccc(Nc3ccc4c(n3)OC(c3ccn[nH]3)CNC4)cc2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 14.26 | [{"value": 14.26, "product": "CC1=NN(C(=C1)C2CN(CC3=C(O2)N=C(C=C3)NC4=CC=C(C=C4)N5C=CN=C5C)CC#N)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-(2-methyl-1H-imidazol-1-yl)aniline (0.121 g, 0.70 mmol), Palladium acetate (0.014 g, 0.06 mmol) and Cesium carbonate (0.618 g, 1.90 mmol) were added in a microwave vial. The mixture was capped and flushed with argon. 2-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonit... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1cc[nH]n1.c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1ncc[nH]1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1.Cc1nccn1-c1ccc(N)cc1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>Cc1cc(C2CN(CC#N)Cc3ccc(Nc4ccc(-n5ccnc5C)cc4)nc3O2)n(C)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-432ccffac1cc473eadf2f2e10de5f379 | Nc1ccc(-n2cncn2)c(Cl)c1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>>OCCN1Cc2ccc(Nc3ccc(-n4cncn4)c(Cl)c3)nc2O[C@H](c2ccccc2)C1 | C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3.C1=CC(=C(C=C1N)Cl)N2C=NC=N2>>C1[C@H](OC2=C(CN1CCO)C=CC(=N2)NC3=CC(=C(C=C3)N4C=NC=N4)Cl)C5=CC=CC=C5 | [NH2:10][c:11]1[cH:12][cH:13][c:14](-[n:15]2[cH:16][n:17][cH:18][n:19]2)[c:20]([Cl:21])[cH:22]1.Cl[c:9]1[cH:8][cH:7][c:6]2[c:24]([n:23]1)[O:25][C@H:26]([c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH2:33][N:4]([CH2:3][CH2:2][OH:1])[CH2:5]2>>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[cH:12][... | Nc1ccc(-n2cncn2)c(Cl)c1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1 | OCCN1Cc2ccc(Nc3ccc(-n4cncn4)c(Cl)c3)nc2O[C@H](c2ccccc2)C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-n5cncn5)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 8.78 | [{"value": 8.78, "product": "C1[C@H](OC2=C(CN1CCO)C=CC(=N2)NC3=CC(=C(C=C3)N4C=NC=N4)Cl)C5=CC=CC=C5", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 3-chloro-4-(1H-1,2,4-triazol-1-yl)aniline (77 mg, 0.39 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (120 mg, 0.39 mmol), Palladium acetate (8.84 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (13.80 mg, 0.04 mmol)and Cesium carbonate (385 mg, 1.18 mmol) were added to a micr... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1nc[nH]n1.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | Nc1ccc(-n2cncn2)c(Cl)c1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>OCCN1Cc2ccc(Nc3ccc(-n4cncn4)c(Cl)c3)nc2O[C@H](c2ccccc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0cc10dc98bd741d3bb43f77d99dd2224 | Ic1ccncc1.Nc1ccnc(Cl)n1>>Clc1nccc(Nc2ccncc2)n1 | C1=CN=CC=C1I.C1=CN=C(N=C1N)Cl>>C1=CN=CC=C1NC2=NC(=NC=C2)Cl | I[c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH2:7])[n:14]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH:7][c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[n:14]1 | Ic1ccncc1.Nc1ccnc(Cl)n1 | Clc1nccc(Nc2ccncc2)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccncn2)ccn1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[#7;a:4]1:[c:5]:[c:6]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:2):[c:2]:[c:3]:1 | 45.34 | [{"value": 45.34, "product": "C1=CN=CC=C1NC2=NC(=NC=C2)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | diacetoxypalladium (0.035 g, 0.15 mmol) was added to a mixture of 2-chloropyrimidin-4-amine (0.250 g, 1.93 mmol), 4-iodopyridine (0.396 g, 1.93 mmol), cesium carbonate (0.755 g, 2.32 mmol) and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.105 g, 0.19 mmol) in 1,4-dioxane (10 mL) and the... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1cncnc1.c1ccncc1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | Ic1ccncc1.Nc1ccnc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe].CC(=O)O.CC(=O)O.[Pd].C1COCCO1>Clc1nccc(Nc2ccncc2)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c3c3446fa521406ab3b5349b3ab1378a | C1COCCN1.Oc1ccc(Br)cc1>>Oc1ccc(N2CCOCC2)cc1 | C1=CC(=CC=C1O)Br.C1COCCN1>>C1COCCN1C2=CC=C(C=C2)O | [NH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1.Br[c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:13][cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[cH:12][cH:13]1 | C1COCCN1.Oc1ccc(Br)cc1 | Oc1ccc(N2CCOCC2)cc1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 31.25 | [{"value": 31.25, "product": "C1COCCN1C2=CC=C(C=C2)O", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-Bromophenol (865 mg, 5 mmol), Tris(dibenzylideneacetone)dipalladium(0) (229 mg, 0.25 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (238 mg, 0.50 mmol), Morpholine (0.437 mL, 5.00 mmol) and sodium tert-butoxide (1009 mg, 10.50 mmol) were stirred in toluene (5 mL) overnight at 100 °C. The mixture... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | C1COCCN1.Oc1ccc(Br)cc1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>Oc1ccc(N2CCOCC2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-decd3260950345c1bc7b269e3329c8ac | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 | C1=CC2=C(C(=C1)Br)OC=C2.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3 | Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][o:19][c:20]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][o:19][c:20]23)[CH2:21][CH2:22]1 | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 84c7e95dd5322b5539d35672e86e91fe517bc82d3c61ab206c2baa800dbd5b66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2occc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1):[c:4](:[c:5]):[#8;a:6]:[c:7] | 84.06 | [{"value": 84.06, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 7-bromobenzofuran (2 g, 10.15 mmol), tert-Butyl 1-piperazinecarboxylate (1.891 g, 10.15 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.465 g, 0.51 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.484 g, 1.02 mmol) and sodium t-butoxide (1.856 mL, 21.32 mmol) were heated to 100 °C in toluene ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-bfb17eeff42440ec958bdd65e83b7c45 | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 | C1=CC2=C(C(=C1)Br)OC=C2.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3 | Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][o:19][c:20]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:21][CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][o:19][c:20]23)[CH2:21][CH2:22]1 | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1 | CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 | CC(C)(C)[O-].[Na+] | CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 84c7e95dd5322b5539d35672e86e91fe517bc82d3c61ab206c2baa800dbd5b66 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2occc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#8;a:6]:[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1):[c:4](:[c:5]):[#8;a:6]:[c:7] | 72.98 | [{"value": 72.98, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2OC=C3", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 7-bromobenzofuran (500 mg, 2.54 mmol), tert-Butyl 1-piperazinecarboxylate (473 mg, 2.54 mmol), Tris(dibenzylideneacetone)dipalladium(0) (116 mg, 0.13 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (121 mg, 0.25 mmol) and sodium t-butoxide (0.464 mL, 5.33 mmol) were heated in toluene (2 mL) to 100 ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2occc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | C1C[NH]CC[NH]1.c1ccc2occc2c1 | HBr | CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | Brc1cccc2ccoc12.CC(C)(C)OC(=O)N1CCNCC1>CC(C)(C)[O-].[Na+].CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(c2cccc3ccoc23)CC1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-69231428717b458492fb802f1da5509b | Nc1ccc(-c2nnc3n2CCC3)cc1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>>OCCN1Cc2ccc(Nc3ccc(-c4nnc5n4CCC5)cc3)nc2O[C@H](c2ccccc2)C1 | C1[C@H](OC2=C(CN1CCO)C=CC(=N2)Cl)C3=CC=CC=C3.C1CC2=NN=C(N2C1)C3=CC=C(C=C3)N>>C1CC2=NN=C(N2C1)C3=CC=C(C=C3)NC4=NC5=C(CN(C[C@H](O5)C6=CC=CC=C6)CCO)C=C4 | [NH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][c:18]3[n:19]2[CH2:20][CH2:21][CH2:22]3)[cH:23][cH:24]1.Cl[c:9]1[cH:8][cH:7][c:6]2[c:26]([n:25]1)[O:27][C@H:28]([c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[CH2:35][N:4]([CH2:3][CH2:2][OH:1])[CH2:5]2>>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][c:6]2[cH:7][cH:8][c:9]([NH:10... | Nc1ccc(-c2nnc3n2CCC3)cc1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1 | OCCN1Cc2ccc(Nc3ccc(-c4nnc5n4CCC5)cc3)nc2O[C@H](c2ccccc2)C1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@@H]2CNCc3ccc(Nc4ccc(-c5nnc6n5CCC6)cc4)nc3O2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:5]:[c:6] | 21.14 | [{"value": 21.14, "product": "C1CC2=NN=C(N2C1)C3=CC=C(C=C3)NC4=NC5=C(CN(C[C@H](O5)C6=CC=CC=C6)CCO)C=C4", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 4-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)aniline (79 mg, 0.39 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (120 mg, 0.39 mmol) Palladium acetate (8.84 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (13.80 mg, 0.04 mmol)and Cesium carbonate (385 mg, 1.18 mmol) wer... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2.c1ccccc1.c1nnc2n1CCC2.c1ccccc1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC | 100 | null | Nc1ccc(-c2nnc3n2CCC3)cc1.OCCN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1>C(=O)([O-])[O-].[Cs+].[Cs+].C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4.CC(=O)O.CC(=O)O.[Pd].COCCOC>OCCN1Cc2ccc(Nc3ccc(-c4nnc5n4CCC5)cc3)nc2O[C@H](c2ccccc2)C1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-50654e3db36e4cb59399fcb1f475b246 | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(I)cc1O>>COC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1O | COC(=O)C1=C(C=C(C=C1)I)O.CC(C)(C)OC(=O)N1CCNCC1>>CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)O | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:23]([OH:24])[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:2... | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(I)cc1O | COC(=O)c1ccc(N2CCN(C(=O)OC(C)(C)C)CC2)cc1O | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 0 | [{"value": 0.0, "product": "CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C(=O)OC)O", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | tert-butyl piperazine-1-carboxylate (0.670 g, 3.60 mmol) and methyl 2-hydroxy-4-iodobenzoate (1 g, 3.60 mmol), BINAP (0.224 g, 0.36 mmol), cesium carbonate (2.461 g, 7.55 mmol) were put inDME (18 mL), tris(dibenzylideneacetone)dipalladium(0) (0.165 g, 0.18 mmol) was added last. Reaction wsa purged by nitrogen, and heat... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC | 90 | null | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1ccc(I)cc1O>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC>COC(=O)c1ccc(N2CC... |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-b57d9ea5b2ca4d5c93ac4813f00278f3 | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=C(C=CC(=C1)F)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([NH:17][c:18]2[cH:19][n:20]([CH3:21])[n:22][c:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16](... | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 67.7 | [{"value": 67.7, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (7.3 g, 19.10 mmol), 2-amino-5-fluoro-N-methoxybenzamide (5.28 g, 28.66 mmol), diacetoxypalladium (0.214 g, 0.96 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.105 g, 1.91 mmol) and cesium carbonate (12.45 g, 38.21 mmol) wer... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-f57bbfadfec74fbbad7d399cf7b15368 | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=C(C=CC(=C1)F)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([NH:17][c:18]2[cH:19][n:20]([CH3:21])[n:22][c:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16](... | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 46.21 | [{"value": 46.21, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 95 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (113 mg, 0.30 mmol), 2-amino-5-fluoro-N-methoxybenzamide (60 mg, 0.33 mmol) and Cesium carbonate (193 mg, 0.59 mmol) in degassed dioxane (4 mL) under nitrogen at room temperature were degassed (nitrogen) for a further 5 minutes before adding Pa... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 95 | null | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-79d988a2695b450ba5f0891b3987351f | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | CC1=NN(C=C1NC2=NC=C(C(=C2)I)C(F)(F)F)C.CONC(=O)C1=C(C=CC(=C1)F)N>>CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH2:13].I[c:14]1[cH:15][c:16]([NH:17][c:18]2[cH:19][n:20]([CH3:21])[n:22][c:23]2[CH3:24])[n:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[NH:13][c:14]1[cH:15][c:16](... | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1 | CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3cn[nH]c3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 58.84 | [{"value": 58.84, "product": "CC1=NN(C=C1NC2=NC=C(C(=C2)NC3=C(C=C(C=C3)F)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-amino-5-fluoro-N-methoxybenzamide (2.60 g, 14.13 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (3.6 g, 9.42 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.545 g, 0.94 mmol) diacetoxypalladium (0.106 g, 0.47 mmol) and cesium carbonate (6.14 g, 18.84 mmol) were su... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cn[nH]c1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CONC(=O)c1cc(F)ccc1N.Cc1nn(C)cc1Nc1cc(I)c(C(F)(F)F)cn1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1cc(F)ccc1Nc1cc(Nc2cn(C)nc2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-7696589313724974b3ed4cfa26a52287 | CNC(=O)c1ccc(F)cc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.CNC(=O)C1=C(C=C(C=C1)F)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH2:12].I[c:13]1[cH:14][c:15]([NH:16][c:17]2[cH:18][c:19]([CH3:20])[n:21][n:22]2[CH3:23])[n:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16][c:17... | CNC(=O)c1ccc(F)cc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 36.19 | [{"value": 36.19, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 2-amino-4-fluoro-N-methylbenzamide (2.310 g, 13.74 mmol), N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (3.5 g, 9.16 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.530 g, 0.92 mmol) diacetoxypalladium (0.103 g, 0.46 mmol) and cesium carbonate (5.97 g, 18.32 mmol) were su... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 100 | null | CNC(=O)c1ccc(F)cc1N.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-172edbc585f4482992d8b345126c6340 | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.COC1=CC=CC(=C1C(=O)NOC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32].I[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][n:18]2[CH3:19])[n:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][c:15]... | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 0 | [{"value": 0.0, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), 2-amino-N,6-dimethoxybenzamide (43.6 mg, 0.22 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (8.15 mg, 0.01 mmol) and cesium carbonate (85 mg, 0.26 mmol) were suspended in 1,4-dio... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-067f9706b99f4ac98e07f49d63946447 | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.COC1=CC=CC(=C1C(=O)NOC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32].I[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][n:18]2[CH3:19])[n:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][c:15]... | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[K+].[K+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 0 | [{"value": 0.0, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), 2-amino-N,6-dimethoxybenzamide (43.6 mg, 0.22 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol) and potassium carbonate (36.2 mg, 0.26 mmol) were s... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[K+].[K+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a7be07888e18485384d8c572f896eab3 | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.COC1=CC=CC(=C1C(=O)NOC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32].I[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][n:18]2[CH3:19])[n:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][c:15]... | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 71.59 | [{"value": 71.59, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (22.8 g, 59.67 mmol), 2-amino-N,6-dimethoxybenzamide (19.90 g, 101.43 mmol), diacetoxypalladium (0.670 g, 2.98 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3.45 g, 5.97 mmol) and cesium carbonate (23.33 g, 71.60 mmol) were s... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-0c382ee82f944b7aad82248930edf86a | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | CC1=NN(C(=C1)NC2=NC=C(C(=C2)I)C(F)(F)F)C.COC1=CC=CC(=C1C(=O)NOC)N>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C | [CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH2:8])[cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32].I[c:9]1[cH:10][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][n:18]2[CH3:19])[n:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][c:13]3[cH:14][c:15]... | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1 | CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]):[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:16](:[c:18]):[c:15]-[C:... | 56.87 | [{"value": 56.87, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C(=CC=C3)OC)C(=O)NOC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (351 mg, 0.92 mmol), 2-amino-N,6-dimethoxybenzamide (270 mg, 1.38 mmol) and Cesium carbonate (598 mg, 1.83 mmol) in degassed dioxane (8 mL) under nitrogen at room temperature were allowed to stir, degassing (nitrogen) for a further 5 minutes be... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HI | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-a11b668f474546c6bffcfc85e307c94b | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1>>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl.CC1=NN(C(=C1)N)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([F:9])[cH:10]2)[c:26]([C:27]([F:28])([F:29])[F:30])[cH:25][n:24]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH3:23]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16]... | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1 | CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 55.5 | [{"value": 55.5, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide (8.9 g, 25.60 mmol), 1,3-dimethyl-1H-pyrazol-5-amine (3.41 g, 30.72 mmol), diacetoxypalladium (0.460 g, 2.05 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.370 g, 4.10 mmol) and cesium carbonate (10.01 g, 30.72 mmol) were ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c8bd9a8a68d6433daf2fe8e0bf9a22b5 | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1>>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | CNC(=O)C1=C(C=C(C=C1)F)NC2=CC(=NC=C2C(F)(F)F)Cl.CC1=NN(C(=C1)N)C>>CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C | Cl[c:15]1[cH:14][c:13]([NH:12][c:11]2[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([F:9])[cH:10]2)[c:26]([C:27]([F:28])([F:29])[F:30])[cH:25][n:24]1.[NH2:16][c:17]1[cH:18][c:19]([CH3:20])[n:21][n:22]1[CH3:23]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH:12][c:13]1[cH:14][c:15]([NH:16]... | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1 | CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccnc(Nc3ccn[nH]3)c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH2;D1;+0:12]>>[C;D1;H3:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 61.74 | [{"value": 61.74, "product": "CC1=NN(C(=C1)NC2=NC=C(C(=C2)NC3=C(C=CC(=C3)F)C(=O)NC)C(F)(F)F)C", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide (2 g, 5.75 mmol), 1,3-dimethyl-1H-pyrazol-5-amine (0.767 g, 6.90 mmol) diacetoxypalladium (0.103 g, 0.46 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.533 g, 0.92 mmol) and cesium carbonate (2.249 g, 6.90 mmol) were suspe... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1cc[nH]n1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1C(F)(F)F.Cc1cc(N)n(C)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNC(=O)c1ccc(F)cc1Nc1cc(Nc2cc(C)nn2C)ncc1C(F)(F)F |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-5a3f171e783f417796d44475a35d5d8d | CS(=O)(=O)c1ccc(N)cc1.Clc1cncc(Cl)n1>>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | C1=C(N=C(C=N1)Cl)Cl.CS(=O)(=O)C1=CC=C(C=C1)N>>CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:17][cH:18]1.Cl[c:10]1[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][n:12][cH:13][c:14]([Cl:15])[n:16]2)[cH:17][cH:18]1 | CS(=O)(=O)c1ccc(N)cc1.Clc1cncc(Cl)n1 | CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10] | 21.95 | [{"value": 21.95, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC2=CN=CC(=N2)Cl", "details": "", "is_desired": true}] | 90 | CELSIUS | null | null | 2,6-dichloropyrazine (287 mg, 1.93 mmol), 4-(methylsulfonyl)aniline (330 mg, 1.93 mmol), diacetoxypalladium (43.3 mg, 0.19 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (120 mg, 0.19 mmol) and cesium carbonate (690 mg, 2.12 mmol) in 1,4-dioxane (2 mL) were degazed and stirred at 90 °C for 16 hours under nitrogen. ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 90 | null | CS(=O)(=O)c1ccc(N)cc1.Clc1cncc(Cl)n1>C(=O)([O-])[O-].[Cs+].[Cs+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CS(=O)(=O)c1ccc(Nc2cncc(Cl)n2)cc1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-11b483655b194597ac2e93597b6914d4 | COc1cccc(Br)c1.N#CC1CCNCC1>>COc1cccc(N2CCC(C#N)CC2)c1 | COC1=CC(=CC=C1)Br.C1CNCCC1C#N>>COC1=CC=CC(=C1)N2CCC(CC2)C#N | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16]1.[NH:8]1[CH2:9][CH2:10][CH:11]([C:12]#[N:13])[CH2:14][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C:12]#[N:13])[CH2:14][CH2:15]2)[cH:16]1 | COc1cccc(Br)c1.N#CC1CCNCC1 | COc1cccc(N2CCC(C#N)CC2)c1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 28.45 | [{"value": 28.45, "product": "COC1=CC=CC(=C1)N2CCC(CC2)C#N", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | Reaction carried out by , work up and purification on this page. piperidine-4-carbonitrile (7.07 g, 64.16 mmol); 1-bromo-3-methoxybenzene (6.77 mL, 53.47 mmol) and diacetoxypalladium (2.401 g, 10.69 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabic... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | COc1cccc(Br)c1.N#CC1CCNCC1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cccc(N2CCC(C#N)CC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-fa6037d0d8a544539857cac2da5223a4 | COc1cccc(Br)c1.N#CC1CCNCC1>>COc1cccc(N2CCC(C#N)CC2)c1 | COC1=CC(=CC=C1)Br.C1CNCCC1C#N>>COC1=CC=CC(=C1)N2CCC(CC2)C#N | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16]1.[NH:8]1[CH2:9][CH2:10][CH:11]([C:12]#[N:13])[CH2:14][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C:12]#[N:13])[CH2:14][CH2:15]2)[cH:16]1 | COc1cccc(Br)c1.N#CC1CCNCC1 | COc1cccc(N2CCC(C#N)CC2)c1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 54.48 | [{"value": 54.48, "product": "COC1=CC=CC(=C1)N2CCC(CC2)C#N", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | piperidine-4-carbonitrile (0.353 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILY... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | COc1cccc(Br)c1.N#CC1CCNCC1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cccc(N2CCC(C#N)CC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-c91f5415f0604adda8f4b73dd97ab0f8 | COc1cccc(Br)c1.NC(=O)C1CCNCC1>>COc1cccc(N2CCC(C(N)=O)CC2)c1 | COC1=CC(=CC=C1)Br.C1CNCCC1C(=O)N>>COC1=CC=CC(=C1)N2CCC(CC2)C(=O)N | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17]1.[NH:8]1[CH2:9][CH2:10][CH:11]([C:12]([NH2:13])=[O:14])[CH2:15][CH2:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH:11]([C:12]([NH2:13])=[O:14])[CH2:15][CH2:16]2)[cH:17]1 | COc1cccc(Br)c1.NC(=O)C1CCNCC1 | COc1cccc(N2CCC(C(N)=O)CC2)c1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C | CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 0 | [{"value": 0.0, "product": "COC1=CC=CC(=C1)N2CCC(CC2)C(=O)N", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | piperidine-4-carboxamide (0.411 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1 | 100 | null | COc1cccc(Br)c1.NC(=O)C1CCNCC1>[Li+].C[Si](C)(C)[N-][Si](C)(C)C.CC(C)CN1CCN2CCN(P1N(CC2)CC(C)C)CC(C)C.CC(=O)O.CC(=O)O.[Pd].CC1=CC=CC=C1>COc1cccc(N2CCC(C(N)=O)CC2)c1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-ced8329d85d843b9adb25a3a7cf2fe09 | CN.O=[N+]([O-])c1ccc2nc(Br)sc2c1>>CNc1nc2ccc([N+](=O)[O-])cc2s1 | C1=CC2=C(C=C1[N+](=O)[O-])SC(=N2)Br.CN>>CNC1=NC2=C(S1)C=C(C=C2)[N+](=O)[O-] | [CH3:1][NH2:2].Br[c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[s:14]1>>[CH3:1][NH:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[s:14]1 | CN.O=[N+]([O-])c1ccc2nc(Br)sc2c1 | CNc1nc2ccc([N+](=O)[O-])cc2s1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 32798d554dc80c085869b4a43a5b4fb6dfd5a087e49c559b1d6e1572d282c401 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2scnc2c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 6.19 | [{"value": 6.19, "product": "CNC1=NC2=C(S1)C=C(C=C2)[N+](=O)[O-]", "details": "", "is_desired": true}] | 150 | CELSIUS | null | null | methanamine (0.793 mL, 19.30 mmol), 2-bromo-6-nitrobenzo[d]thiazole (1 g, 3.86 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.268 g, 0.46 mmol), cesium carbonate (1.886 g, 5.79 mmol) and diacetoxypalladium (0.043 g, 0.19 mmol) were suspended in 1,4-dioxane (8 mL) and sealed into a microwave tube. ... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 150 | null | CN.O=[N+]([O-])c1ccc2nc(Br)sc2c1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>CNc1nc2ccc([N+](=O)[O-])cc2s1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-95b63e9e9ac540bc8fc7f0ffbc5bc6a7 | COc1ccc([N+](=O)[O-])cc1N.Clc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1>>COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1 | C1=CC=C2C(=C1)C(=CN2)C3=NC(=NC=C3Cl)Cl.COC1=C(C=C(C=C1)[N+](=O)[O-])N>>COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=CNC4=CC=CC=C43)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[NH2:12].Cl[c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](-[c:19]2[cH:20][nH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[NH:12][c:13]1[n:14][cH:15][c:16]([Cl:17])[c:18](-... | COc1ccc([N+](=O)[O-])cc1N.Clc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1 | COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1 | C(=O)([O-])[O-].[Cs+].[Cs+] | CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd] | C1COCCO1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3c[nH]c4ccccc34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 0 | [{"value": 0.0, "product": "COC1=C(C=C(C=C1)[N+](=O)[O-])NC2=NC=C(C(=N2)C3=CNC4=CC=CC=C43)Cl", "details": "", "is_desired": true}] | 80 | CELSIUS | null | null | To a stirred solution of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (100 mg, 0.38 mmol) in dioxane (10 mL) was added 2-methoxy-5-nitroaniline (63.7 mg, 0.38 mmol), cesium carbonate (247 mg, 0.76 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.3 mg, 0.05 mmol). The resulting suspension was purged w... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2[nH]ccc2c1 | HCl | C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1 | 80 | null | COc1ccc([N+](=O)[O-])cc1N.Clc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1>C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C.CC(=O)O.CC(=O)O.[Pd].C1COCCO1>COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2c[nH]c3ccccc23)n1 |
ord_dataset-00005539a1e04c809a9a78647bea649c | ord-916b542fdcc44d6284100092f1e92c3f | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2>>COc1nc(Nc2cc(C)c3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)Cl.CN1C=C(C=N1)C2=C(N=C(C=C2)N)OC>>CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC | [CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[cH:25][cH:26][c:27]1-[c:28]1[cH:29][n:30][n:31]([CH3:32])[cH:33]1.Cl[c:7]1[cH:8][c:9]([CH3:10])[c:11]2[c:12]([n:13]1)[O:14][CH:15]([CH2:16][C:17]([F:18])([F:19])[F:20])[CH2:21][N:22]([CH3:23])[CH2:24]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]3[c:12]([n:... | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2 | COc1nc(Nc2cc(C)c3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1 | CC(C)(C)[O-].[Na+] | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 392582ab1e0d1e44e1eb41cf86502459310432dd2113eece0fc86616425d0995 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(n2)OCCNC3)ncc1-c1cn[nH]c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#8:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[#8:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]):[c:5]:[c:6] | 9.77 | [{"value": 9.77, "product": "CC1=CC(=NC2=C1CN(CC(O2)CC(F)(F)F)C)NC3=NC(=C(C=C3)C4=CN(N=C4)C)OC", "details": "", "is_desired": true}] | 100 | CELSIUS | null | null | 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (104 mg, 0.51 mmol), 8-chloro-4,6-dimethyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (150 mg, 0.51 mmol), Sodium tert-butoxide (73.4 mg, 0.76 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (22.19 mg, 0.04 mmol) and Tris(dibenzyli... | null | https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471 | Aromatic halide.Primary amine | Secondary amine | c1cnc2c(c1)C[NH]CCO2 | c1cnc2c(c1)C[NH]CCO2 | c1ccncc1.c1cnc2c(c1)C[NH]CCO2.c1cn[nH]c1 | HCl | CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1 | 100 | null | COc1nc(N)ccc1-c1cnn(C)c1.Cc1cc(Cl)nc2c1CN(C)CC(CC(F)(F)F)O2>CC(C)(C)[O-].[Na+].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC1=CC=CC=C1>COc... |
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