1-Methylindole → HCID 57936241, compound

Participants

Reaction Steps

A solution of 1-methyl-indole (244 mg, 1.86 mmol) in 10 ml of THF was treated with n-butyllithium (0.74 ml of a 2.5M solution in hexanes, 1.86 mmol) at −78° C. and the mixture was stirred under argon for 2 hours. In the meantime, a solution of (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (250 mg, 0.93 mmol) in 10 ml of THF was treated with n-butyllithium (0.74 ml of 2.5M solution in hexanes, 1.86 mmol) at −78° C. under argon for 15 minutes and the above solution containing the lithiated 1-methyl-indole was added with a syringe. The reaction mixture was stirred for 15 minutes at 0° C. and for 2 hours at room temperature. The reaction was quenched with saturated ammonium chloride solution (5 ml) and extracted with EtOAc. The organic layer was dried over sodium sulfate and evaporated. Purification by column chromatography on silicagel (EtOAc/MeOH/ammonia:2/1/0.02) gave the title compound. Yield: 92.5 mg (27%).

Provenance & Evidence