Sodium hydride → HCID 58365107, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-piperidin-3-ol hydrogen chloride (169 mg, 1.2 mmol) in tetrahydrofuran (4.5 mL) and N,N-dimethylformamide (1 mL) was added sodium hydride as 60% dispersion in mineral oil (200 mg, 5.0 mmol). The reaction mixture was stirred at ambient temperature for 5 minutes before 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (200 mg, 0.56 mmol) was added in one portion and the reaction mixture was stirred at this temperature for 10 minutes before being warmed to 40° C. for 4 hours. The cooled reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as a yellow solid, which was used in the next step without any further purification (236 mg, 100%).

Provenance & Evidence