Hydrochloric Acid → HCID 67271478, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-cyclopropyl-5-methoxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (355 mg, 1.01 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (472 mg, 2.20 mmol), tetrakis(triphenylphosphene)palladium (87 mg, 0.075 mmol), aqueous sodium carbonate (2 M, 3.0 mL, 6.00 mmol), DMF (5.9 mL) and ethanol (5.9 mL) is heated under nitrogen at 85° C. for 4 h. The mixture is acidified with 1 N HCl and extracted with ethyl acetate. The ethyl acetate layers are combined and washed with water and brine and dried over MgSO4. The residue is purified via flash chromatography eluting with THF-heptane (25→40%) to afford the title compound (187 mg, 49%) as a white solid. ES/MS m/e 380.0 (M+1).

Provenance & Evidence