(3-Methylpyridin-4-yl)boronic acid--hydrogen chloride (1/1) → HCID 71535817, compound

Participants

Reaction Steps

Using the conditions of General Procedure C 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; 111 mg, 0.25 mmol) was reacted with 3-picoline-4-boronic acid hydrochloride salt (available from Combi-Blocks Inc.; 87 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(3-methyl-pyridin-4-yl)-benzoic acid (46 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ 13.30 (br s, 1H), 8.59-8.66 (m, 2H), 8.50 (s, 1H), 8.30-8.38 (m, 2H), 8.10 (dd, J=8.5, 1.9 Hz, 1H), 7.88-7.94 (m, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.56-7.63 (m, 1H), 7.52 (d, J=8.1 Hz, 1H), 2.34 (s, 3H).

Provenance & Evidence