Dimethylformamide → HCID 44223229, compound

Participants

Reaction Conditions

Reaction Steps

2,6-Difluoro-N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.025 g, 0.0379 mmol) and Cu(I)CN (0.0678 g, 0.758 mmol) were taken up in DMF (0.5 mL) and heated to 100° C. overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil, N-(3-cyano-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide. The oil (0.021 g, 0.038 mmol) was dissolved in MeOH (1.0 mL) and water (0.3 mL). K2CO3 (0.053 g, 0.38 mmol) was added, and the mixture stirred for 1 hour at room temperature. The solution was partitioned between water and EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (5% MeOH/DCM) giving N-(3-cyano-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (2.9 mg, 18%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 11.16 (s, 1H), 8.57-8.58 (m, 1H), 8.52-8.53 (m, 1H), 8.47 (s, 1H), 7.53-7.59 (m, 1H), 7.25-7.29 (m, 1H), 3.09-3.13 (m, 2H), 1.74-1.80 (m, 2H), 0.98-1.01 (m, 3H); m/z (APCI-neg) M−1=418.2.

Provenance & Evidence