Triphenylphosphine → HCID 10340509, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (243 mg, 0.92 mmol) in methylene chloride (3 mL) cooled to 0° C. was treated with N-bromosuccinimide (165 mg, 0.92 mmol). This solution was stirred at 0° C. for 15 min. At this time, the reaction was treated with 6-chloro-1-isopropyl-1H-indole-3-carboxylic acid (200 mg, 0.84 mmol). This solution was stirred at 0° C. for 15 min and then was allowed to warm to 25° C. where it was stirred for 30 min. The reaction was then treated with 2-amino-5-bromopyridine (363 mg, 2.10 mmol) and was stirred at 25° C. for 10 d. At this time, the reaction was diluted with water (50 mL) and ethyl acetate (50 mL). This mixture was treated with a saturated aqueous sodium bicarbonate solution (25 mL). The organic layer was separated and was washed with a saturated aqueous sodium chloride solution (1×25 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 3/1 hexanes/ethyl acetate) afforded 6-chloro-1-isopropyl-1H-indole-3-carboxylic acid (5-bromo-pyridin-2-yl)-amide (100 mg, 30%) as an off-white foam: mp 57-64° C.; EI-HRMS m/e calcd for C17H15BrClN3O (M+) 391.0087, found 391.0092.

Provenance & Evidence