Potassium Carbonate → 1-(Cyclohexanecarbonyl)indoline-5-sulfonamide

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To a solution of indoline-5-sulfonamide (Intermediate 54A, 100 mg, 0.50 mmol) in MeCN (5.0 mL) was added cyclohexanecarbonyl chloride (0.14 mL, 1.00 mmol) and K2CO3 (174 mg, 1.26 mmol). The resulting reaction mixture was stirred at room temperature overnight and then diluted with EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with 1 N aq. NaOH solution, followed by 10% aq. LiCl solution. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the title compound (31 mg, 20%) as a white solid. 1H NMR (DMSO-d6) δ 8.16 (d, J=6.8 Hz, 1H), 7.64-7.60 (m, 2H), 7.19 (m, 2H), 4.22 (t, J=8.5 Hz, 2H), 3.21-3.16 (m, 2H), 2.62-2.55 (m, 1H), 1.91-1.65 (m, 5H), 1.45-1.16 (m, 5H); MS(ESI+) m/z 309.1 (M+H)+.

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