2-Chloro-5-fluorobenzeneboronic acid → HCID 74221632, compound

Participants

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-fluorophenylboronic acid (available from Combi-Blocks Inc.; 87 mg, 0.5 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′-fluoro-biphenyl-2-carboxylic acid (12 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H), 8.55 (d, J=1.7 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=1.9 Hz, 1H), 8.29 (dd, J=8.1, 1.9 Hz, 1H), 8.09 (dd, J=8.5, 2.1 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.56 (dd, J=8.6, 5.7 Hz, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.30 (d, J=8.7 Hz, 2H).

Provenance & Evidence