4-Chlorobenzaldehyde → HCID 44223172, compound

Participants

Reaction Steps

KOH (0.012 g, 0.22 mmol) was added to 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.37 mL, 0.074 mmol) in MeOH (0.4 mL), followed by the addition of 4-chlorobenzaldehyde (0.013 g, 0.096 mmol). The reaction mixture was stirred at room temperature overnight. The contents were then diluted with EtOAc and NH4Cl (aq.) and extracted with EtOAc (3×). The organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified via column chromatography (5% MeOH/DCM) to afford N-(3-((4-chlorophenyl)(hydroxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (23 mg, 58%). 1H NMR (400 MHz, CD3OD) δ 8.41-8.42 (m, 1H), 8.28-8.29 (m, 1H), 7.60-7.67 (m, 1H), 7.46-7.49 (m, 2H), 7.34-7.36 (m, 2H), 7.09-7.14 (m, 1H), 6.06 (s, 1H), 3.09-3.13 (m, 2H), 1.82-1.91 (m, 2H), 1.03-1.07 (m, 3H); m/z (APCI-pos) M+1=535.1.

Provenance & Evidence