1,1'-Biphenyl-4-yl-boronic acid → Methyl 4-[(4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 412982Notes

Reaction equation

HRID 412982 reaction equation
CSC1SC(C(OC)=O)=CC=1N[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.[NH2:25][C:26]1[CH:27]=[C:28]([C:32]([O:34][CH3:35])=[S:33])[S:29][C:30]=1[CH3:31].C1(C2C=CC(B(O)O)=CC=2)C=CC=CC=1>>[C:16]1([C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26]3[CH:27]=[C:28]([C:32]([O:34][CH3:35])=[S:33])[S:29][C:30]=3[CH3:31])=[CH:23][CH:24]=2)[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 18537271Methyl 5-methylthio-4-[(4-phenylphenyl)amino]thiophene-2-carboxylateHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583857Methyl 4-[(4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylateYield 19.1%

Procedure

Methyl 5-methylthio-4-[(4-phenylphenyl)amino]thiophene-2-carboxylate: Using a procedure similar to Example 208, step (a), 74.4 mg (0.36 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate was allowed to react with 142.5 mg (2 equiv, 0.72 mmol) of 4-phenylphenyl boronic acid to give 24.5 mg (19.1%) of methyl 4-[(4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 2.45 (s, 3H), 3.92 (s, 3H), 6.38 (bs, 1H), 7.08-7.14 (m, 2H), 7.33 (m, 1H), 7.43-7.46 (m, 2H), 7.54-7.60 (m, 411), 7.82 (s, 1H).

Sources & evidence

ORD record
ord-ebd3e7c961764c3cb1b5805f9db4e89d
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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