Water → HCID 45275570, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carbonitrile E48 (90 mg, 0.35 mmol) in THF (1.5 mL), at −78° C., was added a 1M solution of LDA in THF (0.38 mL, 0.38 mmol). The mixture was stirred for 30 min at −78° C. before warming to r.t. After 60 min, methyl iodide (31 μL, 0.5 mmol) was added. The mixture was stirred for a further 60 min at r.t. for 1 h, before addition of water (5 mL). The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to dryness. The crude product was purified by flash column chromatography on silica gel (hexane, EtOAc, 100:0-80:20, biotage 25+M) to furnish the title compound as a white solid (34 mg, 36%), along with recovered 1-(3,5-dichloropyridin-4-yl)piperidine-4-carbonitrile (23 mg, 25%), LC-MS (ESI, 4 min) Rt 3.09 min, m/z 270 (100%, W); m/z (ESI) C12H13Cl2N3 requires 269.0487 found [M+H]+ 289.0488.

Provenance & Evidence