Chlorosuccinimide → 6-Bromo-3-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

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Reaction Steps

NCS (48 mg, 0.361 mmol) was added to a solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.361 mmol) in DMF (1.1 mL). The reaction mixture was stirred overnight at room temperature before being filtered on an SCX-2 column and concentrated under vacuum. The residue was purified via Biotage silica gel column chromatography eluting with (DCM/EtOH 99/1 to 95/5) to afford the title product as a white solid (86 mg, 76%). 1H NMR (500 MHz, CD3OD) δ 4.01 (s, 3H), 7.54 (d, J=0.8 Hz, 1H), 8.05 (s, 1H), 8.28 (s, 1H), 8.47 (d, J=0.8 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 2.84 min, 312 [(M+H+), 100%].

Provenance & Evidence