Sodium hydride → HCID 66571463, compound

Participants

Reaction Conditions

Reaction Steps

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) dissolved in 0.5 mL of DMF was added to a suspension of sodium hydride (7.99 mg, 0.200 mmol) in 1.0 mL of DMF. The reaction was heated at 70° C. for ten minutes before adding 2-methoxyethyl 4-methylbenzenesulfonate (0.144 mL, 0.266 mmol). The reaction was allowed to stir overnight. After 18 hours, the reaction was cooled to room temperature before diluting with water and ethyl acetate. The organic phase was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via column chromatography using 50-80% ethyl acetate/hexanes. The purification provided product as a white solid 1H-NMR (400 MHz, DMSO-d6) 7.63-7.49, 7.43-7.14, 7.12-7.03, 6.67-6.58, 4.68, 4.63-4.06, 3.53, 3.20-3.13, 3.10-2.92, 2.79, 1.92-1.50

Provenance & Evidence