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

HRID 2298674Notes

Reaction equation

HRID 2298674 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=1[CH3:7].[C:12]1([C:18]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:18]2[CH:19]=[CH:20][C:21]([NH:1][C:2]3[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=3[CH3:7])=[CH:22][CH:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583857Methyl 4-[(4-phenylphenyl)amino]-5-methylthiothiophene-2-carboxylateYield 20%

Procedure

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) δ2.45 (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, 4H), 7.82 (s, 1H).

Sources & evidence

ORD record
ord-46902cfbe03342b580af5145b9b70b86
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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