Potassium Carbonate → HCID 67114429, compound

Participants

Reaction Conditions

Reaction Steps

A 1.0 M aqueous potassium carbonate solution (9.96 mL, 9.96 mmol) was added to a mixture of 3-bromo-1-(phenylsulfonyl)-1H-indol-6-amine (1.00 g, 2.84 mmol), (4-nitrophenyl)boronic acid (1.19 g, 7.12 mmol) and palladium tetrakis(triphenylphosphine) (164 mg, 0.14 mmol) in tetrahydrofuran (13.7 mL). The biphasic mixture was heated in a microwave at 130° C. for 10 min and was then diluted with a saturated solution of sodium bicarbonate (10.0 mL) and ethyl acetate (10.0 mL). The organic layer was washed with a saturated solution of sodium bicarbonate (2×10.0 mL), and the combined aqueous layers were extracted with ethyl acetate (3×30.0 mL). The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by flash chromatography (10-25-50-71% ethyl acetate/hexane) to give an orange solid for 3-(4-nitrophenyl)-1-(phenylsulfonyl)-1H-indol-6-amine (726 mg, 1.85 mmol, 65%).

Provenance & Evidence