Styrylboronic acid → 2-(2-Chlorophenylamino)-3,4-difluoro-6-styrylbenzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (0.313 g, 0.271 mmol) and trans-2-phenylvinylboronic acid (1.105 g, 7.468 mmol) were added to a mixture of 6-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.00 g, 5.31 mmol) in 35 mL DME and 8 mL 2.0 M aqueous K2CO3 solution. The reaction mixture was heated under a N2 atmosphere to 90° C. and stirred for 16 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and water and the layers separated. The organic layer was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography gave 1.20 g (56%) clean desired product.

Provenance & Evidence