N-bromobutanimide → N-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide

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Reaction Steps

2,6-Difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.500 g, 1.268 mmol) was charged to a 100 mL round-bottom flask. CHCl3 (25 mL) was added to form a slurry. N-Bromosuccinimide (0.271 g, 1.52 mmol) was added and stirred for 20 minutes. The reaction mixture was filtered, washed with DCM, and dried under vacuum providing N-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.427 g, 71.2%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 12.12 (br s, 1H), 11.04 (s, 1H), 9.81 (br s, 1H), 8.41-8.43 (m, 1H), 8.34-8.35 (m, 1H), 7.74-7.76 (m, 1H), 7.53-7.59 (m, 1H), 7.25-7.30 (m, 1H), 3.11-3.15 (m, 2H), 1.75-1.80 (m, 2H), 0.98-1.02 (m, 3H); m/z (APCI-pos) M+1=473.0, 475.0.

Provenance & Evidence