Dimethylformamide → HCID 86671898, compound

Participants

Reaction Steps

sodium hydride (12.78 mg, 0.320 mmol) was added to an oven dried flask and placed under nitrogen. It was then suspended in 1.0 mL of DMF. The suspension was placed in a 70° C. oil bath before adding N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) as a 0.5 mL DMF solution. The reaction was allowed to stir for 20 minutes before the addition of 3-bromoprop-1-yne (0.047 ml, 0.533 mmol) dropwise. The reaction was allowed to stir overnight. The reaction was cooled and diluted with saturated ammonium chloride and ethyl acetate. The organic layer was washed with saturated ammonium chloride followed by saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The yellow crude material was purified via Biotage column 30-70% ethyl acetate:hexanes 4 gram silicycle column to obtain white solid. (Yield: 50 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.64-7.53, 7.40-7.05, 6.75-6.65, 5.16-5.04, 4.65, 4.58-3.99, 3.23, 3.10-2.93, 2.76, 1.85-1.52

Provenance & Evidence