Potassium Carbonate → 1-(2-(3,4-Dichlorophenyl)acetyl)indoline-5-sulfonamide

Participants

Reaction Steps

To a suspension of 2-(3,4-dichlorophenyl)acetic acid (137 mg, 0.67 mmol) in DCE (2.0 mL) was added oxalyl chloride (908 μL, 1.82 mmol, 2.0M solution in CH2Cl2) (0.908 mL, 1.816 mmol) followed by one drop of DMF. The resulting reaction mixture was stirred at room temperature for 40 min and then concentrated in vacuo. To a solution of the crude residue in MeCN (4.0 mL) was added indoline-5-sulfonamide (120 mg, 0.61 mmol) and K2CO3 (167 mg, 1.21 mmol). The reaction mixture was stirred at room temperature for 1 h. Additional indoline-5-sulfonamide (40 mg, 0.20 mmol) was added, and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was then diluted with EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with 10% aq. LiCl solution and then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the title compound (180 mg, 77%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.11 (d, J=8.4 Hz, 1H), 7.59 (m, 4H), 7.29 (dd, J=8.1, 2.0 Hz, 1H), 7.22 (s, 2H), 4.26 (t, J=8.5 Hz, 2H), 3.94 (s, 2H), 3.24 (t, J=8.5 Hz, 2H); MS(ESI+) m/z 385.0 (M+H)+.

Provenance & Evidence