Water → HCID 11574511, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-5-(3-methoxybenzoyl)-4-methyl-4,5-dihydropyrrolo[1,2-a]quinoxaline (240 mg, 0.60 mmol) and tetrabutylammonium iodide (558 mg, 1.51 mmol) in methylene chloride (5 mL) at −78° C., under nitrogen, was treated with a 1 M solution of boron trichloride in methylene chloride (1.51 mL, 1.51 mmol). The reaction was then warmed to 0° C. and was stirred for 4 h. Ice and water was added to the reaction which was stirred to 30 min. The reaction was then diluted with a saturated aqueous solution of sodium bicarbonate, and the product was extracted with methylene chloride (3×25 mL). The product was purified via Biotage Horizon® (25S, silica, gradient from 15% EtOAc/hexane to 60% EtOAc/hexane) to yield 196 mg (85%) of 3-[(7-bromo-4-methylpyrrolo[1,2-a]quinoxalin-5(4H)-yl)carbonyl]phenol as a white foam. MS (ESI) m/z 383/385 ([M+H]+); MS (ESI) m/z 381/383 ([M−H]−); HRMS: calcd for C19H15BrN2O2, 382.0317; found (ESI+), 383.03805.

Provenance & Evidence