2-Chloro-5-(trifluoromethyl)phenylboronic acid → 4-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2'-nitro-5'-trifluoromethyl-biphenyl-2-carboxylic acid

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Reaction Steps

Using the conditions of General Procedure A 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 2-chloro-5-(trifluoromethyl)phenylboronic acid (2-nitro-5-trifluoromethylphenylboronic acid, pinacol ester (available from Combi-Blocks Inc.; 117 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-nitro-5′-trifluoromethyl-biphenyl-2-carboxylic acid (31 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ 13.48 (s, 1H), 8.55 (d, J=1.7 Hz, 1H), 8.51 (s, 1H), 8.29-8.37 (m, 2H), 8.24 (d, J=8.3 Hz, 1H), 8.10 (dd, J=8.4, 2.0 Hz, 1H), 8.03 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H).

Provenance & Evidence