Hydrochloric Acid → HCID 178485317, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-N-methylbenzamide (16.0 g) in THF (180 ml) was slowly added dropwise a solution (1.6 M; 103 ml) of n-butyllithium in hexane at −78° C., and the mixture was stirred at −78° C. for 20 min. Trimethoxyborane (50.2 ml) was added dropwise at −78° C. and the mixture was stirred at −78° C. for 30 min and at room temperature for 17 h. 2N Hydrochloric acid (82.0 ml) was added to the reaction mixture, and after stirring for 1 h, the reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give a crude product (22.5 g) of 3-[(methylamino)carbonyl]phenylboronic acid as a pale-yellow oil. By the reaction in the same manner as in Example 29-(i) using this product (19.2 g), (4-bromophenyl)(1-trityl-1H-imidazol-4-yl)methanone (10.0 g), 2M aqueous sodium carbonate solution (81.2 ml) and tetrakis(triphenylphosphine)palladium(0) (1.17 g), the title compound (6.89 g) was obtained as colorless powder crystals.

Provenance & Evidence