2-Methoxypyridine-3-boronic acid hydrate → 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(2-methoxy-pyridin-3-yl)-benzoic 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 and 2-methoxypyridine-3-boronic acid hydrate (available from Combi-Blocks Inc.; 68 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(2-methoxy-pyridin-3-yl)-benzoic acid (11 mg, 12%). 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 8.47 (s, 1H), 8.41 (d, J=1.9 Hz, 1H), 8.33 (d, J=2.1 Hz, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.18 (dd, J=5.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.1 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.70 (dd, J=7.3, 1.8 Hz, 1H), 7.52 (d, J=7.9 Hz, 1H), 7.10 (dd, J=7.2, 5.1 Hz, 1H), 3.78 (s, 3H).

Provenance & Evidence