Sodium Bicarbonate → HCID 22676778, compound

Participants

Reaction Steps

tert-Butyl 3(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]sulfonyl}indole-2-carboxylate (Example 27, 45 mg, 0.085 mmol) was dissolved in trifluoroacetic acid (0.4 mL). The resulting mixture was allowed to stir for 5 minutes. The reaction mixture was treated with a saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate (3×4 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 3-(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]sulfonyl}indole-2-carboxylic acid as an oil (17 mg, 42%): 1H (acetone-d6) δ 3.70 (s, 3 H), 6.85-6.89 (m, 2 H), 7.20-7.34 (m, 2 H), 7.47 (dd, J=0.6, 8.1 Hz, 1 H), 7.60-7.68 (m, 3 H), 7.83 (br d, 1 H), 8.06 (d, J=8.2 Hz, 1 H), 8.63 (m, 2 H); mass spectroscopy HPLC ES MS m/z (rel abundance) 476 ((M+H)+, 48%).

Provenance & Evidence