Aluminum(III) Chloride → 7-Chloro-3-(2-chlorophenethyl)-5-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

7-Chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-5-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (50 mg) was dissolved in anisole (2.1 mL) and aluminum chloride (46 mg, 4 eq) was added. The reaction was stirred at 85° C. for 2 h, then poured into ice:EtOAc (1:1). The quenched reaction was stirred vigorously for 1 h, then the organic layer was separated, washed with brine, dried over sodium sulfate, and then concentrated onto silica gel and purified by chromatography (gradient: DCM to 9:1 DCM:MeOH) delivering product (10 mg, 25% yield). HRMS (ES+) m/z calcd for C23H17Cl2N5O2 [M+H]+, 466.0838. found, 466.0838.

Provenance & Evidence