3-(2,3-dihydro-1H-indole-1-sulfonyl)benzoic acid synthesis

Yield:327092-69-3 33%

Reaction Conditions:

with sodium hydrogencarbonate in water; pH=8; for 2 h;

Steps:

To a mixture of 3-(chlorosulfonyl)benzoic acid (220 mg, 1.01 mmol), water (30 mL) and indoline (120 mg, 1.01 mmol) was added NaHC0₃ to adjust the pH of the mixture to 8. After stirred for 2 hours, the mixture was added HC1 until pH = 3, then concentrated in vacuo, and filtered to yield a white product, which was purified by recrystallization in ethanol to afford 41 (100 mg, 33%) as a white solid. *H NMR (500 MHz, CD30D): δ 2.92 (t, J = 8.0 Hz, 2H), 3.98 (t, J = 8.0 Hz, 2H), 7.00 (t, J = 7.4 Hz, 1H), 7.09 (d, J = 7.4 Hz, 1H), 7.23 (t, J = 7.8 Hz, 1H), 7.57 (t, J = 7.8 Hz, 1H), 7.65 (t, J =8.1 Hz, 1H), 8.01 (d, J = 7.9 Hz, 1H), 8.27 (d, J = 7.8 Hz, 1H), 8.54 (s, 1H).

References:

WO2015/157504,2015,A1 Location in patent:Page/Page column 31