1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Participants

Reaction Steps

1H-Pyrrolo[2,3-b]pyridin-5-amine (9.97 g, 74.88 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (23.00 g, 82.37 mmol), EDCI (15.79 g, 82.37 mmol), and HOBt (11.13 g, 82.37 mmol) were charged to a 2 L round-bottomed flask. DMF was added to give a homogeneous solution, and the reaction mixture was stirred at room temperature overnight. The solution was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed with water (3×), brine, dried over Na2SO4 and concentrated to a slurry. DCM (500 mL) was added to this slurry, and the mixture was reconcentrated. Additional DCM (500 mL) was added, and the slurry was filtered, washed with DCM and dried under vacuum providing 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (15.49 g, 52.5%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 11.65 (br s, 1H), 10.85 (s, 1H), 9.79 (br s, 1H), 8.34-8.37 (m, 2H), 7.51-7.57 (m, 1H), 7.48-7.50 (m, 1H), 6.46-6.48 (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=395.1.

Provenance & Evidence