(2-Acetylthiophen-3-yl)boronic acid → HCID 86679861, compound

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-acetyl-3-thienylboronic acid (available from Aldrich Chemical Company, Inc.; 68 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2-(2-acetyl-thiophen-3-yl)-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid (19 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 13.12 (br s, 1H), 8.52 (d, J=1.8 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.94 (d, J=5.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.10 (d, J=5.0 Hz, 1H), 2.08 (s, 3H).

Provenance & Evidence