Chlorosuccinimide → HCID 86689841, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (517.0 mg, 3.23 mmol) in anhydrous DMF (5.0 mL) at 0° C. was added a solution of NCS (462.0 mg, 3.39 mmol) dissolved in anhydrous DMF (10 mL). The reaction mixture was stirred at 0° C. for 1 h and then at RT for 18 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with sat'd. aq. NaHCO3 solution, water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with EtOAc/heptane. Recovered product was crystallized from DCM to afford 600 mg (95.5%) of 1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 11.96 (br s, 1H), 8.01 (d, J=2.9 Hz, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 2.71 (s, 3H); MS (ESI) m/z: 195.2 [M+1]+.

Provenance & Evidence