6-Methoxypyridine-2-boronic acid → 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(6-methoxy-pyridin-2-yl)-benzoic acid

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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 6-methoxypyridine-2-boronic acid (available from Combi-Blocks Inc.; 61 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-(6-methoxy-pyridin-2-yl)-benzoic acid (23 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ 12.95 (br s, 3H), 8.48 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.21 (dd, J=4.3, 2.3 Hz, 2H), 8.10 (dd, J=8.3, 2.0 Hz, 1H), 7.73-7.94 (m, 3H), 7.39 (d, J=7.3 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 3.88 (s, 3H), 2.54 (s, 9H).

Provenance & Evidence