Tetrabutylammonium Fluoride → HCID 90421732, compound

Participants

Reaction Steps

To a solution of Intermediate 6-chloro-5-(6-dimethylamino-2-methoxy-pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-indole-3-carboxylic acid methyl ester (109 g, 212 mmol) in THF (1000 mL) at room temperature was added tetrabutylammonium fluoride (1.0 M in THF, 400 mL, 400 mmol). The reaction was stirred at reflux for 3 h before cooling to room temperature and diluting with ethyl acetate (2000 mL). This was washed with sat. aq. NaHCO3 (2×750 mL), sat. aq. NH4Cl (2×750 mL), water (750 mL), and brine (750 mL), and then dried over MgSO4, filtered, and concentrated in vacuo. The residue was triturated with methanol (˜500 mL) and filtered. The solids were washed with methanol (300 mL) and suction dried overnight to afford desired product (71.8 g, 94%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ=11.99 (s, 1 H) 8.13 (s, 1 H) 7.82 (s, 1 H) 7.57 (s, 1 H) 7.32 (d, J=8.20 Hz, 1 H) 6.22 (d, J=8.20 Hz, 1 H) 3.78 (s, 3 H) 3.76 (s, 3 H) 3.07 (s, 6 H); MS (ES+) 360.1 (M+H)+.

Provenance & Evidence