Ethyl Acetate → methyl 6-chloro-5-{4-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-1H-indole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.311 mmol), 4-(3-(4-bromophenoxy)propyl)morpholin-3-one (100 mg, 0.373 mmol), 2N potassium carbonate (0.5 mL, 2 mmol), and Pd(dppf)Cl2 (30 mg, 0.03 mmol) in toluene/ethanol (1.44 mL/0.48 mL) was stirred at 110° C. for 2.5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated to give a residue, which was purified by preparative TLC to give the title compound (50 mg, 50% yield) as a white solid.

Provenance & Evidence