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SchwallerGroup
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uspto_50_suzuki

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mech_smi_ori
stringlengths
240
351
rxn_idx
int64
0
39
step_idx_retro
int64
0
6
source
stringclasses
26 values
source_db
stringclasses
1 value
split
stringclasses
1 value
rxn_length
int64
7
7
step_idx_forward
int64
0
6
equ_with_last_step
bool
1 class
mech_smi_equ
stringlengths
240
351
elem_reac_equ
stringlengths
227
321
elem_prod_equ
stringlengths
230
321
mech_smi_min
stringlengths
56
245
elem_reac_min
stringlengths
43
215
elem_prod_min
stringlengths
46
215
elem_reac_spe
stringlengths
104
398
rxn_prod_equ
stringclasses
40 values
rxn_prod_min
stringclasses
40 values
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+].[Pd:1]|(2, 1)
21
6
reaction_0
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]|(1, 2)
21
5
reaction_0
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C:1]1[Cl:2].O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]|(3, 1);((1, 2), 3)
21
4
reaction_0
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C:1]1[Cl:2].O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([Cl])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=[C:1]1[Cl:2]|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1Cl
COC(=O)C1=CC=CN=[C]1[Pd-2]([Cl])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[Cl:3].O=C([O-])[O-:4].OB(O)C1=CC=CC(Br)=C1.[Na+:1].[Na+]|(4, 2);((2, 3), 1)
21
3
reaction_0
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[Cl:3].O=C([O-])[O-:4].OB(O)C1=CC=CC(Br)=C1.[Na+:1].[Na+]|(4, 2);((2, 3), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([Cl])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OB(O)C1=CC=CC(Br)=C1.[Na+].[Na][Cl]
COC(=O)C1=CC=CN=[C]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[Cl:3].O=C([O-])[O-:4].[Na+:1]|(4, 2);((2, 3), 1)
COC(=O)C1=CC=CN=[C]1[Pd-2]([Cl])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].[Na+]
COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.COC(=O)C1=CC=CN=[C]1[Pd-2]([Cl])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O[B:3](O)[C:1]1=CC=CC(Br)=C1.[Na+].[Na][Cl]|(2, 1);((1, 3), 2)
21
2
reaction_0
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O[B:3](O)[C:1]1=CC=CC(Br)=C1.[Na+].[Na][Cl]|(2, 1);((1, 3), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OB(O)C1=CC=CC(Br)=C1.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Na+].[Na][Cl]
COC(=O)C1=CC=CN=[C]1[Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O[B:3](O)[C:1]1=CC=CC(Br)=C1|(2, 1);((1, 3), 2)
COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.OB(O)C1=CC=CC(Br)=C1
COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([B:1](O)O)[O:3]C(=O)[O-].[Na+].[Na][Cl]|((2, 3), 1);((1, 2), 2)
21
1
reaction_0
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2:2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([B:1](O)O)[O:3]C(=O)[O-].[Na+].[Na][Cl]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
COC(=O)C1=CC=CN=[C]1[Pd-2:2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([B:1](O)O)[O:3]C(=O)[O-]|((2, 3), 1);((1, 2), 2)
COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
COC(=O)C1=CC=CN=[C]1[Pd-2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.COC(=O)C1=CC=CN=[C]1[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C:1]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]|((2, 1), 3);((3, 2), 2)
21
0
reaction_0
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C:1]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]|((2, 1), 3);((3, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=[C]1[Pd-2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
COC(=O)C1=CC=CN=[C:1]1[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=CC=CC(Br)=C1|((2, 1), 3);((3, 2), 2)
COC(=O)C1=CC=CN=[C]1[Pd-2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1Cl.COC(=O)C1=CC=CN=[C]1[Pd-2]([C]1=CC=CC(Br)=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC(Br)=C1.[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CCO.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC(=O)C1=CC=CN=C1C1=CC=CC(Br)=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+].[Pd:2]|(1, 2)
0
6
reaction_12
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+].[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
0
5
reaction_12
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C:1]([I:2])C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
0
4
reaction_12
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C:1]([I:2])C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2]([I])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1CCCC(N2N=[C:1]([I:2])C3=C(N)N=CN=C32)C1|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1
CN1CCCC(N2N=[C]([Pd-2]([I])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2:1]([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[I:4])C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-:2].[Na+:3].[Na+]|(2, 1);((1, 4), 3)
0
3
reaction_12
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2:1]([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[I:4])C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-:2].[Na+:3].[Na+]|(2, 1);((1, 4), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2]([I])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.[Na+].[Na][I]
CN1CCCC(N2N=[C]([Pd-2:1]([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[I:4])C3=C(N)N=CN=C32)C1.O=C([O-])[O-:2].[Na+:3]|(2, 1);((1, 4), 3)
CN1CCCC(N2N=[C]([Pd-2]([I])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.O=C([O-])[O-].[Na+]
CN1CCCC(N2N=[C]([Pd-2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.CN1CCCC(N2N=[C]([Pd-2]([I])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C:1]([B:3]4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.[Na+].[Na][I]|(2, 1);((1, 3), 2)
0
2
reaction_12
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C:1]([B:3]4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.[Na+].[Na][I]|(2, 1);((1, 3), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([O]C(=O)[O-])([B]4OC(C)(C)C(C)(C)O4)([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
CC1=CC(C)=C2OC(NC3=CC=[C:1]([B:3]4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1|(2, 1);((1, 3), 2)
CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=[C]([Pd-2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1
CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([O]C(=O)[O-])([B]4OC(C)(C)C(C)(C)O4)([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.CN1CCCC(N2N=[C]([Pd-2]([O]C(=O)[O-])([P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)[P+](C3=CC=CC=C3)(C3=CC=CC=C3)C3=CC=CC=C3)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2:2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([B:1]4OC(C)(C)C(C)(C)O4)[O:3]C(=O)[O-])C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
0
1
reaction_12
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2:2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([B:1]4OC(C)(C)C(C)(C)O4)[O:3]C(=O)[O-])C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([O]C(=O)[O-])([B]4OC(C)(C)C(C)(C)O4)([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2:2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([B:1]4OC(C)(C)C(C)(C)O4)[O:3]C(=O)[O-])C=C3)=NC2=C1|((2, 3), 1);((1, 2), 2)
CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([O]C(=O)[O-])([B]4OC(C)(C)C(C)(C)O4)([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1
CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([O]C(=O)[O-])([B]4OC(C)(C)C(C)(C)O4)([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
0
0
reaction_12
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
CC1=CC(C)=C2OC(NC3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C54)C=C3)=NC2=C1|((2, 3), 1);((1, 2), 2)
CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3)=NC2=C1.CC1=CC(C)=C2OC(NC3=CC=[C]([Pd-2]([C]4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3)=NC2=C1.CN1CCCC(N2N=C(I)C3=C(N)N=CN=C32)C1.COCCOC.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC(C)=C2OC(NC3=CC=C(C4=NN(C5CCCN(C)C5)C5=NC=NC(N)=C45)C=C3)=NC2=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+].[Pd:2]|(1, 2)
8
6
reaction_14
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+].[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
34
6
reaction_14
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:1])C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]|(2, 1)
8
5
reaction_14
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:1])C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:1])C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
34
5
reaction_14
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=N[C:1]([Cl:2])=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]|(3, 1);((1, 2), 3)
8
4
reaction_14
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=N[C:1]([Cl:2])=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=N[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(C=O)C(NC2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=N[C:1]([Cl:2])=C(C=O)C(NC2=CC=CC=C2)=N1|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1
CSC1=N[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(C=O)C(NC2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(Cl)=C(C=O)C(NC2=CC=CC=C2)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C:1]([Cl:2])=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
34
4
reaction_14
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C:1]([Cl:2])=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([Cl])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C:1]([Cl:2])=N4)CC3)C=C1)=N2|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2
CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([Cl])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=NC(Cl)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:4])=N1.O.O=C([O-])[O-:1].OB(O)C1=CC=CC=C1.[K+:2].[K+]|(1, 3);((3, 4), 2)
8
3
reaction_14
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:4])=N1.O.O=C([O-])[O-:1].OB(O)C1=CC=CC=C1.[K+:2].[K+]|(1, 3);((3, 4), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.OB(O)C1=CC=CC=C1.[Cl][K].[K+]
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:4])=N1.O=C([O-])[O-:1].[K+:2]|(1, 3);((3, 4), 2)
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O=C([O-])[O-].[K+]
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.[Cl][K]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:2]([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[Cl:3])=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-:4].[Na+:1].[Na+]|(4, 2);((2, 3), 1)
34
3
reaction_14
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:2]([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[Cl:3])=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-:4].[Na+:1].[Na+]|(4, 2);((2, 3), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([Cl])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]
CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:2]([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[Cl:3])=N4)CC3)C=C1)=N2.O=C([O-])[O-:4].[Na+:1]|(4, 2);((2, 3), 1)
CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([Cl])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.O=C([O-])[O-].[Na+]
CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([Cl])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O[B:2](O)[C:1]1=CC=CC=C1.[Cl][K].[K+]|(3, 1);((1, 2), 3)
8
2
reaction_14
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O[B:2](O)[C:1]1=CC=CC=C1.[Cl][K].[K+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.OB(O)C1=CC=CC=C1.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.[Cl][K].[K+]
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:3]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O[B:2](O)[C:1]1=CC=CC=C1|(3, 1);((1, 2), 3)
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.OB(O)C1=CC=CC=C1
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[Cl][K].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C:1](C)[B:2](O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:3]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]|(3, 1);((1, 2), 3)
34
2
reaction_14
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C:1](C)[B:2](O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:3]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=NC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=C(O4)C(C(C)C)=CC(C#N)=C5)C=C3)CC2)=CC=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]
C=[C:1](C)[B:2](O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2:3]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2|(3, 1);((1, 2), 3)
C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2
C=[C](C)[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=NC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=C(O4)C(C(C)C)=CC(C#N)=C5)C=C3)CC2)=CC=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=C(C)B(O)O.CC(C)C1=CC(C#N)=CC2=C1OC(C1=CC=C(C(=O)NCC3CCN(C4=CC=N[C]([Pd-2]([O]C(=O)[O-])([P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)[P+](C5=CC=CC=C5)(C5=CC=CC=C5)C5=CC=CC=C5)=N4)CC3)C=C1)=N2.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=N1.O.[Cl][K].[K+]|((2, 3), 1);((1, 2), 2)
8
1
reaction_14
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=N1.O.[Cl][K].[K+]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2:2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=N1|((2, 3), 1);((1, 2), 2)
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[Cl][K].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2:1]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([O:2]C(=O)[O-])[B:3](O)O.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
34
1
reaction_14
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2:1]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([O:2]C(=O)[O-])[B:3](O)O.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C=[C](C)[Pd-2:1]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([O:2]C(=O)[O-])[B:3](O)O|((1, 2), 3);((3, 1), 1)
C=[C](C)[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C=[C](C)[Pd-2]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=[C](C)[Pd-2]([O]C(=O)[O-])([B](O)O)([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]|((2, 1), 3);((3, 2), 2)
8
0
reaction_14
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]|((2, 1), 3);((3, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2)=N1|((2, 1), 3);((3, 2), 2)
CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)[C]([Pd-2]([C]2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[Cl][K].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(C2=CC=CC=C2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C:1](C)[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]|((2, 3), 1);((1, 2), 2)
34
0
reaction_14
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C:1](C)[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=[C](C)[Pd-2]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C=[C:1](C)[Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[C:3]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1|((2, 3), 1);((1, 2), 2)
C=[C](C)[Pd-2]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.C=[C](C)[Pd-2]([C]1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC1=CC=CC=C1.CCO.CSC1=NC(NC2=CC=CC=C2)=C(C=O)C(Cl)=N1.O.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1.CC1=CC=CC=C1.CCO.O.O=C([O-])OB(O)O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C=C(C)C1=NC=CC(N2CCC(CNC(=O)C3=CC=C(C4=NC5=CC(C#N)=CC(C(C)C)=C5O4)C=C3)CC2)=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+].[Pd:1]|(2, 1)
9
6
reaction_17
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
16
6
reaction_17
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=C(C=C(Br)C=C3)CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd:2].[Pd]|(1, 2)
39
6
reaction_17
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=C(C=C(Br)C=C3)CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd:2].[Pd]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=C(C=C(Br)C=C3)CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=C(C=C(Br)C=C3)CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=C(C=C(Br)C=C3)CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]|(1, 2)
9
5
reaction_17
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
16
5
reaction_17
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]|(1, 2)
39
5
reaction_17
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C:3]([I:1])=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]|(2, 3);((3, 1), 2)
9
4
reaction_17
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C:3]([I:1])=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]|(2, 3);((3, 1), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([I])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C:3]([I:1])=C(Cl)C=C1C(=O)O|(2, 3);((3, 1), 2)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(I)=C(Cl)C=C1C(=O)O
COC1=C[C]([Pd-2]([I])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C:2]([Cl:3])=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2);((2, 3), 1)
16
4
reaction_17
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C:2]([Cl:3])=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2);((2, 3), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=C[C:2]([Cl:3])=CC=N1|(1, 2);((2, 3), 1)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(Cl)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C:1]([Br:2])C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]|(3, 1);((1, 2), 3)
39
4
reaction_17
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C:1]([Br:2])C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([Br])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=[C:1]([Br:2])C=C3CCC12|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([Br])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=C(Br)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[I:2])=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-:3].OB(O)C1=CC=CC=C1Cl.[K+:4].[K+]|(3, 1);((1, 2), 4)
9
3
reaction_17
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[I:2])=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-:3].OB(O)C1=CC=CC=C1Cl.[K+:4].[K+]|(3, 1);((1, 2), 4)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([I])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.OB(O)C1=CC=CC=C1Cl.[K+].[K][I]
COC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[I:2])=C(Cl)C=C1C(=O)O.O=C([O-])[O-:3].[K+:4]|(3, 1);((1, 2), 4)
COC1=C[C]([Pd-2]([I])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.O=C([O-])[O-].[K+]
COC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.[K][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.COC1=C[C]([Pd-2]([I])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-:4].[Na+:3].[Na+]|(4, 1);((1, 2), 3)
16
3
reaction_17
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-:4].[Na+:3].[Na+]|(4, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])=CC=N1.O=C([O-])[O-:4].[Na+:3]|(4, 1);((1, 2), 3)
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.O=C([O-])[O-].[Na+]
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[Br:2])C=C3CCC12.ClCCl.O=C([O-])[O-:3].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+:4].[Na+].[Pd]|(3, 1);((1, 2), 4)
39
3
reaction_17
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[Br:2])C=C3CCC12.ClCCl.O=C([O-])[O-:3].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+:4].[Na+].[Pd]|(3, 1);((1, 2), 4)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([Br])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na][Br].[Pd]
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[Br:2])C=C3CCC12.O=C([O-])[O-:3].[Na+:4]|(3, 1);((1, 2), 4)
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([Br])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.O=C([O-])[O-].[Na+]
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.[Na][Br]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([Br])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O[B:2](O)[C:3]1=CC=CC=C1Cl.[K+].[K][I]|(1, 3);((3, 2), 1)
9
2
reaction_17
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O[B:2](O)[C:3]1=CC=CC=C1Cl.[K+].[K][I]|(1, 3);((3, 2), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.OB(O)C1=CC=CC=C1Cl.[K+].[K][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.[K+].[K][I]
COC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.O[B:2](O)[C:3]1=CC=CC=C1Cl|(1, 3);((3, 2), 1)
COC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.OB(O)C1=CC=CC=C1Cl
COC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)O[B:2]([C:3]2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]|(1, 3);((3, 2), 1)
16
2
reaction_17
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)O[B:2]([C:3]2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]|(1, 3);((3, 2), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CCOC(C)=O.O.[Na+].[Na][Cl]
CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)O[B:2]([C:3]2=CC(F)=CC=C2O)OC1(C)C|(1, 3);((3, 2), 1)
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(C2=CC(F)=CC=C2O)OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=CC1=C[C:1]([B:3](O)O)=CC=C1O.OBO.[Na+].[Na][Br].[Pd]|(2, 1);((1, 3), 2)
39
2
reaction_17
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=CC1=C[C:1]([B:3](O)O)=CC=C1O.OBO.[Na+].[Na][Br].[Pd]|(2, 1);((1, 3), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=CC1=CC(B(O)O)=CC=C1O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.OBO.[Na+].[Na][Br].[Pd]
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.O=CC1=C[C:1]([B:3](O)O)=CC=C1O|(2, 1);((1, 3), 2)
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.O=CC1=CC(B(O)O)=CC=C1O
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].O=CC1=CC(B(O)O)=CC=C1O.OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)=C(Cl)C=C1C(=O)O.Cl.[K+].[K][I]|((1, 2), 3);((3, 1), 1)
9
1
reaction_17
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2:1]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)=C(Cl)C=C1C(=O)O.Cl.[K+].[K][I]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.[K+].[K][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
COC1=C[C]([Pd-2:1]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)=C(Cl)C=C1C(=O)O|((1, 2), 3);((3, 1), 1)
COC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O
COC1=C[C]([Pd-2]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3]2OC(C)(C)C(C)(C)O2)=CC=N1.CCOC(C)=O.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
16
1
reaction_17
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3]2OC(C)(C)C(C)(C)O2)=CC=N1.CCOC(C)=O.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
CC(C)(C)OC(=O)NC1=C[C]([Pd-2:1]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3]2OC(C)(C)C(C)(C)O2)=CC=N1|((1, 2), 3);((3, 1), 1)
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([O:2]C(=O)[O-])[B:3](O)O)C=C3CCC12.ClCCl.OBO.[Na+].[Na][Br].[Pd]|((1, 2), 3);((3, 1), 1)
39
1
reaction_17
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([O:2]C(=O)[O-])[B:3](O)O)C=C3CCC12.ClCCl.OBO.[Na+].[Na][Br].[Pd]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2:1]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([O:2]C(=O)[O-])[B:3](O)O)C=C3CCC12|((1, 2), 3);((3, 1), 1)
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]|((2, 3), 1);((1, 2), 2)
9
0
reaction_17
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=C[C]([Pd-2]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O|((2, 3), 1);((1, 2), 2)
COC1=C[C]([Pd-2]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.COC1=C[C]([Pd-2]([C]2=CC=CC=C2Cl)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[K][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(C)C=O.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O.Cl.O=C([O-])OB(O)O.[K+].[K][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=CC=CC=C2Cl)=C(Cl)C=C1C(=O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C:3]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
16
0
reaction_17
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C:3]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
CC(C)(C)OC(=O)NC1=C[C:3]([Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC(F)=CC=C2O)=CC=N1|((1, 2), 3);((3, 1), 1)
CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=C[C]([Pd-2]([C]2=CC(F)=CC=C2O)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.CN(C)C=O.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.[K+].[Na+].[Na][Cl].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1COCCO1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1.CC1(C)OB(OC(=O)[O-])OC1(C)C.CCOC(C)=O.O.[Na+].[Na][Cl]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)NC1=CC(C2=CC(F)=CC=C2O)=CC=N1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]|((2, 1), 3);((3, 2), 2)
39
0
reaction_17
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]|((2, 1), 3);((3, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
CN1C(=O)CCC2(C)C3=CC=[C:1]([Pd-2:2]([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[C:3]4=CC=C(O)C(C=O)=C4)C=C3CCC12|((2, 1), 3);((3, 2), 2)
CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(C)C=O.CN1C(=O)CCC2(C)C3=CC=[C]([Pd-2]([C]4=CC=C(O)C(C=O)=C4)([P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)[P+](C4=CC=CC=C4)(C4=CC=CC=C4)C4=CC=CC=C4)C=C3CCC12.COC1=CC(I)=C(Cl)C=C1C(=O)O.Cl.ClCCl.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1Cl.OBO.[K+].[Na+].[Na][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12.ClCCl.O=C([O-])OB(O)O.OBO.[Na+].[Na][Br].[Pd]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN1C(=O)CCC2(C)C3=CC=C(C4=CC=C(O)C(C=O)=C4)C=C3CCC12
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
27
6
reaction_18
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
27
5
reaction_18
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C:1]([I:2])=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
27
4
reaction_18
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C:1]([I:2])=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2]([I])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.NC1=NC=NC2=C1[C:1]([I:2])=NN2C1=CC=[N+]([O-])C=C1|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1
NC1=NC=NC2=C1[C]([Pd-2]([I])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.NC1=NC=NC2=C1C(I)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[I:3])=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-:4].[Na+:1].[Na+]|(4, 2);((2, 3), 1)
27
3
reaction_18
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[I:3])=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-:4].[Na+:1].[Na+]|(4, 2);((2, 3), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2]([I])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.[Na+].[Na][I]
NC1=NC=NC2=C1[C]([Pd-2:2]([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[I:3])=NN2C1=CC=[N+]([O-])C=C1.O=C([O-])[O-:4].[Na+:1]|(4, 2);((2, 3), 1)
NC1=NC=NC2=C1[C]([Pd-2]([I])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O=C([O-])[O-].[Na+]
NC1=NC=NC2=C1[C]([Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.NC1=NC=NC2=C1[C]([Pd-2]([I])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C:1]([B:3]2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.[Na+].[Na][I]|(2, 1);((1, 3), 2)
27
2
reaction_18
USPTO_suzuki
train
7
4
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C:1]([B:3]2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.[Na+].[Na][I]|(2, 1);((1, 3), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=NC=NC2=C1[C]([Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=C2C(N)=NC=N3)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
COC1=C[C:1]([B:3]2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.NC1=NC=NC2=C1[C]([Pd-2:2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1|(2, 1);((1, 3), 2)
COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.NC1=NC=NC2=C1[C]([Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1
COC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=C2C(N)=NC=N3)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.NC1=NC=NC2=C1[C]([Pd-2]([O]C(=O)[O-])([P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=NN2C1=CC=[N+]([O-])C=C1.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C]([Pd-2:2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1]2OC(C)(C)C(C)(C)O2)[O:3]C(=O)[O-])=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
27
1
reaction_18
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C]([Pd-2:2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1]2OC(C)(C)C(C)(C)O2)[O:3]C(=O)[O-])=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=C[C]([Pd-2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
COC1=C[C]([Pd-2:2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1]2OC(C)(C)C(C)(C)O2)[O:3]C(=O)[O-])=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C|((2, 3), 1);((1, 2), 2)
COC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=C[C]([Pd-2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COC1=C[C]([Pd-2]([O]C(=O)[O-])([B]2OC(C)(C)C(C)(C)O2)([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]|((2, 1), 3);((3, 2), 2)
27
0
reaction_18
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]|((2, 1), 3);((3, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=C[C]([Pd-2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
COC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C32)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C|((2, 1), 3);((3, 2), 2)
COC1=C[C]([Pd-2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COC1=C[C]([Pd-2]([C]2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.NC1=C2C(I)=NN(C3=CC=[N+]([O-])C=C3)C2=NC=N1.O.O=C([O-])[O-].[Na+].[Na][I].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1(C)OB(OC(=O)[O-])OC1(C)C.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C.COCCOC.O.[Na+].[Na][I]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC(C2=NN(C3=CC=[N+]([O-])C=C3)C3=NC=NC(N)=C23)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+].[Pd:1]|(2, 1)
7
6
reaction_19
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+].[Pd:2]|(1, 2)
19
6
reaction_19
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+].[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:2]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.COCCOC.O.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.OB(O)C1=CC=CC=C1F.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]|(1, 2)
7
5
reaction_19
USPTO_suzuki
train
7
1
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]|(1, 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:2])C=C1.C1=CC=C([P:1](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(1, 2)
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C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
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19
5
reaction_19
USPTO_suzuki
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1
true
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C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:1])C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.COCCOC.O.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.OB(O)C1=CC=CC=C1F.[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Pd]
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C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:2]2[Cl:3])CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]|(1, 2);((2, 3), 1)
7
4
reaction_19
USPTO_suzuki
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7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:2]2[Cl:3])CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]|(1, 2);((2, 3), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:1][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:2]2[Cl:3])CC1|(1, 2);((2, 3), 1)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C:1]([Br:2])=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+]|(3, 1);((1, 2), 3)
19
4
reaction_19
USPTO_suzuki
train
7
2
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C:1]([Br:2])=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+]|(3, 1);((1, 2), 3)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([Br])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.[K+].[K+]
C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-2:3][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=C[C:1]([Br:2])=CS1)C(=O)C1=CC=CC=C1|(3, 1);((1, 2), 3)
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1
CN(CC1=C[C]([Pd-2]([Br])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC1=CC=CC=C1.CN(CC1=CC(Br)=CS1)C(=O)C1=CC=CC=C1.COCCOC.O.O=C([O-])[O-].O=CC1=CC=C(B(O)O)C=C1.OB(O)C1=CC=CC=C1F.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])CC1.COCCOC.O.O=C([O-])[O-:3].OB(O)C1=CC=CC=C1F.[K+:4].[K+]|(3, 1);((1, 2), 4)
7
3
reaction_19
USPTO_suzuki
train
7
3
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])CC1.COCCOC.O.O=C([O-])[O-:3].OB(O)C1=CC=CC=C1F.[K+:4].[K+]|(3, 1);((1, 2), 4)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.OB(O)C1=CC=CC=C1F.[Cl][K].[K+]
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[Cl:2])CC1.O=C([O-])[O-:3].[K+:4]|(3, 1);((1, 2), 4)
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.O=C([O-])[O-].[K+]
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.[Cl][K]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([Cl])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
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19
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reaction_19
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7
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reaction_19
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.OB(O)C1=CC=CC=C1F.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.[Cl][K].[K+]
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.O[B:2](O)[C:3]1=CC=CC=C1F|(1, 3);((3, 2), 1)
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.OB(O)C1=CC=CC=C1F
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
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19
2
reaction_19
USPTO_suzuki
train
7
4
true
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.[K+].[K][Br]
CN(CC1=C[C]([Pd-2:1]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=CC1=CC=[C:2]([B:3](O)O)C=C1|(1, 2);((2, 3), 1)
CN(CC1=C[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=CC1=CC=C(B(O)O)C=C1
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C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)CC1.COCCOC.O.[Cl][K].[K+]|((1, 2), 3);((3, 1), 1)
7
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reaction_19
USPTO_suzuki
train
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)CC1.COCCOC.O.[Cl][K].[K+]|((1, 2), 3);((3, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2:1]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([O:2]C(=O)[O-])[B:3](O)O)CC1|((1, 2), 3);((3, 1), 1)
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[Cl][K].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2:2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=CS1)C(=O)C1=CC=CC=C1.[K+].[K][Br]|((2, 3), 1);((1, 2), 2)
19
1
reaction_19
USPTO_suzuki
train
7
5
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2:2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=CS1)C(=O)C1=CC=CC=C1.[K+].[K][Br]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.[K+].[K][Br]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
CN(CC1=C[C]([Pd-2:2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([B:1](O)O)[O:3]C(=O)[O-])=CS1)C(=O)C1=CC=CC=C1|((2, 3), 1);((1, 2), 2)
CN(CC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1
CN(CC1=C[C]([Pd-2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([O]C(=O)[O-])([B](O)O)([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.COCCOC.O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:3]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]|((1, 3), 2);((2, 1), 1)
7
0
reaction_19
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:3]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]|((1, 3), 2);((2, 1), 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C:3]2[Pd-2:1]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:2]2=CC=CC=C2F)CC1|((1, 3), 2);((2, 1), 1)
CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=[C]2[Pd-2]([C]2=CC=CC=C2F)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CC1.COCCOC.O.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[Cl][K].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1.COCCOC.O.O=C([O-])OB(O)O.[Cl][K].[K+]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2C2=CC=CC=C2F)CC1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]|((2, 3), 1);((1, 2), 2)
19
0
reaction_19
USPTO_suzuki
train
7
6
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]|((2, 3), 1);((1, 2), 2)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
CN(CC1=C[C:1]([Pd-2:2]([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[C:3]2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1|((2, 3), 1);((1, 2), 2)
CN(CC1=C[C]([Pd-2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC(C)(C)OC(=O)N1CCN(C2=CC=CN=C2Cl)CC1.CC1=CC=CC=C1.CN(CC1=C[C]([Pd-2]([C]2=CC=C(C=O)C=C2)([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=CS1)C(=O)C1=CC=CC=C1.COCCOC.O.O=C([O-])OB(O)O.O=C([O-])[O-].OB(O)C1=CC=CC=C1F.[K+].[K][Br].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CN(CC1=CC(C2=CC=C(C=O)C=C2)=CS1)C(=O)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+].[Pd:1]|(2, 1)
23
6
reaction_2
USPTO_suzuki
train
7
0
true
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+].[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd:1]|(2, 1)
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.[Pd]
[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[Pd]
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=CC=C(C2=CC(C=O)=C3CCCC3=C2OC)C=C1.O.O=C([O-])OB(O)O.[K+].[K][Br]
C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC=C(C2=CC(C=O)=C3CCCC3=C2OC)C=C1
C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+](C2=CC=CC=C2)(C2=CC=CC=C2)[Pd-:1])C=C1.C1=CC=C([P:2](C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+]|(2, 1)
23
5
reaction_2
USPTO_suzuki
train
7
1
true
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=C(Br)C=C(C=O)C2=C1CCC2.COC1=CC=C(B(O)O)C=C1.O.O=C([O-])[O-].[K+].[K+].[Pd-][P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
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23
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reaction_2
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=CC=C(C2=CC(C=O)=C3CCCC3=C2OC)C=C1.O.O=C([O-])OB(O)O.[K+].[K][Br]
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23
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reaction_2
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C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.C1=CC=C(P(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.CC1=CC=CC=C1.COC1=CC=C(B(O)O)C=C1.COC1=[C]([Pd-2]([O]C(=O)[O-])([P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=O)C2=C1CCC2.O.[K+].[K][Br]
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23
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reaction_2
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C1=CC=C([P+]([Pd-2][P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1.COC1=CC=C(C2=CC(C=O)=C3CCCC3=C2OC)C=C1
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Collection including SchwallerGroup/uspto_50_suzuki