2-Chloro-5-hydroxybenzeneboronic acid → 2'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-hydroxy-biphenyl-2-carboxylic 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 2-chloro-5-hydroxybenzeneboronic acid (available from Combi-Blocks Inc.; 69 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5′-hydroxy-biphenyl-2-carboxylic acid (71 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ 13.01 (br s, 1H), 9.76 (s, 1H), 8.48 (s, 2H), 8.34 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.5 Hz, 1H), 6.78 (dd, J=8.7, 2.9 Hz, 1H), 6.71 (d, J=2.8 Hz, 1H).

Provenance & Evidence