4-Chlorophenylboronic acid → Methyl 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 2298671Notes

Reaction equation

HRID 2298671 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].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:1][C:2]2[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=2[CH3:7])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583852Methyl 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylateYield 12.4%

Procedure

Using a procedure similar to Example 208, step (a), 66.6 mg (0.32 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate was allowed to react with 100 mg (2 equiv, 0.64 mmol) of 4-chlorophenyl boronic acid to give 11.8 mg (11.7%) of methyl 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylate and 21 mg (31.5%) of unreacted starting material. 1H NMR (CDCl3, 400 MHz) δ2.41 (s, 3H), 3.89 (s, 3H), 6.09 (bs, 1H), 6.94 (d, 2H, J=8.6 Hz), 7.25 (d, 2H, J=8.6 Hz), 7.70 (s, 1H).

Sources & evidence

ORD record
ord-80fcf64fd0d540d89bf8eb073f5aec4f
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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