Potassium Carbonate → 3-Ethyl-2-isopropenyl-5-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

A 100 ml reaction flask equipped with a stirring bar and thermocouple are charged with Pd(OAc)2 (56 mg, 0.25 mmol), DtBPF (142 mg, 0.3 mmol), 2-chloro-4-methylaniline (0.71 g, 5 mmol), 2-methyl-1-hexen-3-yne (0.94 g, 10 mmol), K2CO3 (1.73 g, 12.5 mmol) and DMF (50 mL). The flask was purged with argon. The reaction was heated to 110° C. and stirred overnight. The reaction was complete after 20 h at 110° C. The mixture was filtered through a layer of diatomaceous earth and washed with EtOAc (10 mL). The filtrate was diluted with water (50 mL), extracted with EtOAc (100 mL×3). The combined organic phase was washed with water (50 mL×4) and brine, dried over MgSO4, filtered and concentrated to give a dark brown residue. The product was purified via chromatography on silica gel (hexane/EtOAc 50/1). The desired product was obtained as an off-white solid (0.6 g, 60%).

Provenance & Evidence