Chlorosuccinimide → HCID 45274281, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (100 mg, 0.35 mmol) in DMF (7.00 mL) was added N-chlorosuccinimide (94 mg, 0.70 mmol). The reaction was heated to 80° C. and stirred for 8 hours before partitioning between EtOAc and water (100 ml each), the separated organic layer was washed with water (2×75 ml), brine (20 mL), dried (MgSO4) and concentrated under reduced pressure to give a crude clear pale yellow oil (82 mg). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 98:2-84:16, biotage 25+S) followed by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 14+M) to give a mixture of title compound and 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide by-product as a white solid (20 mg). The mixture was further purified by preparative hplc (MeOH, H2O, 9:20, 25 min) to furnish the title compound as a white solid, LC-MS (ESI, 4 min) Rt 2.46 min, m/z 320 (100%, [M+H]+); m/z (ESI) C11H13N3OClBr requires 316.9931, found [M+H]+ 318.0003.

Provenance & Evidence