1-Fluoro-2,6-dichloropyridinium triflate (31 mg, 0.1 mmol) was added to 2,6-difluoro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (39 mg, 0.1 mmol) in MeCN (4 mL). The mixture was heated at 60° C. for 18 hours and then cooled to room temperature. The mixture was then diluted with EtOAc, washed with brine, dried over MgSO4 and concentrated. The crude product was purified using silica gel chromatography (ISCO) using 5% MeOH in CH2Cl2 as eluent, and subsequently reverse phase HPLC to give 2,6-difluoro-N-(3-fluoro-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (10.7 mg, 26%). 1H NMR (400 MHz, d6-DMSO) δ 11.51 (s, 3H), 10.97 (s, 3H), 9.77 (s, 3H), 8.41 (s, 6H), 7.70-7.38 (m, 6H), 7.26 (t, J=8.5, 3H), 3.45-2.96 (m, 32H), 2.50 (s, 57H), 2.36-2.09 (m, 1H), 1.77 (dd, J=7.5, 15.1, 6H), 1.00 (t, J=7.4, 9H); m/z (LC-MS) M+1=413.4.
