(2-Aminocarbonylphenyl)boronic acid → 2'-Carbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid

Participants

Reaction Steps

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with 2-aminocarbonylphenylboronic acid (available from Combi-Blocks Inc.; 66 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-carbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (15 mg, 8%). 1H NMR (300 MHz, DMSO-d6) δ 13.07 (br s, 1H), 8.46 (s, 1H), 8.36 (d, J=14.1 Hz, 2H), 8.04-8.18 (m, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.58 (d, J=7.2 Hz, 2H), 7.42-7.51 (m, 2H), 7.12-7.34 (m, 3H). The compound of Example 81 has the same formula as the compound of Example 113.

Provenance & Evidence