Methyl Benzoate → HCID 11327913, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of i-PrMgCl in THF (10 mL, 20 mmol) was added 2-bromopyridine (1.93 g, 20.2 mmol) at room temperature in one portion. The mixture was stirred at 35° C. for 0.5 h. To the deep-red solution was added ZnBr2 (4.50 g, 20 mmol) under argon and the resulting mixture was stirred at 70° C. for 0.5 h to obtain a thick white slurry. 1-Methyl-2-pyrrolidinone (20 mL) was added and followed by methyl benzoate (2.5 mL, 20 mmol). The mixture was stirred at 70° C. for 0.5 h. The mixture was cooled to room temperature. Palladium acetate (56.1 mg, 0.25 mmol), 2-dicyclohexylphosphinobiphenyl (350.5 mg, 1 mmol) and 1-[(2-chloro-3-cyclopentyl-1-methyl-1H-indole-6-carbonyl)-amino]-cyclobutanecarboxylic acid methyl ester (1.944 g, 5 mmol) were added. The mixture was stirred at 90° C. until no starting material was left (˜4 h) as monitored by HPLC. The ratio of the coupling product and the starting material was estimated to be 78/22 by HPLC.

Provenance & Evidence