(4-Chloro-2-fluorophenyl)boronic acid → HCID 86679874, compound

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 4-chloro-2-fluorophenylboronic acid (available from Combi-Blocks Inc.; 70 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-fluoro-biphenyl-2-carboxylic acid (0.6 mg, 0.3%). The same compound was also prepared using the conditions of General Procedure C for Suzuki Coupling and Hydrolysis in Parallel Mode when 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 4-chloro-2-fluorophenylboronic acid (available from Combi-Blocks Inc.; 87 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-fluoro-biphenyl-2-carboxylic acid (63.6 mg, 53%). The second sample was characterized by 1H NMR: (300 MHz, DMSO-d6) δ 13.22 (br s, 1H), 8.50 (d, J=4.9 Hz, 2H), 8.26-8.37 (m, 2H), 8.09 (d, J=8.3 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.37-7.60 (m, 4H).

Provenance & Evidence