Potassium Carbonate → HCID 57678938, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 5-bromo-1-(4-methoxy-benzenesulfonyl)-1H-indol-3-ol (21, 130 mg, 0.340 mmol) in acetonitrile (3.5 mL) in a high pressure reaction vessel was added potassium carbonate (235 mg, 1.70 mmol) and bromoacetic acid methyl ester (38.6 μL, 0.408 mmol). The vessel was flushed with a nitrogen atmosphere, sealed with a Teflon stopcock and heated to 80° C. for overnight. After the reaction mixture was cooled to 25° C., ethyl acetate was added and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated at reduced pressure to obtain a light brown solid. Purification of the crude material was carried out using biotage chromatography (30% ethyl acetate in hexanes) which afforded the product as an off-white solid (22, 72.0 mg, 47% yield). MS(ESI) [M+H+]+=454.2; 456.2.

Provenance & Evidence