Bromine → HCID 89871715, compound

Participants

Reaction Steps

An ice cold mixture of methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate (383 mg, 0.940 mmol) in N,N-dimethylformamide (DMF) (5.0 mL) was treated slowly with a solution of bromine (0.053 mL, 1.034 mmol) in dichloromethane (dichloromethane) (280 μl) to give an orange solution. The ice bath was removed and the mixture, which was excluded from light by wrapping the reaction vessel with aluminum foil, was stirred at ambient temperature overnight. The mixture was cooled to 0° C., quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (0-50% ethyl acetate/hexanes gradient) to give the impure desired product as a white solid. The solid was re-purified by reverse phase chromatography to afford the desired product as a white solid (128 mg, 28%). LC/MS (m/z) ES+=486 (M+1).

Provenance & Evidence