Potassium Hydroxide → 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylic Acid

Participants

Reaction Steps

Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate (11.7 g, 35.1 mmol) was dissolved in 350 ml of 1:1 THF/MeOH and 175 ml of 2N KOH (10 eq, 351 mmol). The mixture was stirred at RT for 18 hr. Then the solvents were evaporated under reduced pressure. 2N HCl was added (pH=3) and the aqueous phase was extracted 3× with DCM. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and then concentrated under reduced pressure. 1H NMR (500 MHz, DMSO-d6): δ 12.85 (bs, 1H), 7.80 (d, 1H), 7.60 (m, 3H), 7.50 (m, 1H), 7.10 (t, 1H), 7.00 (d, 2H), 6.70 (d, 1H), 5.80 (s, 2H).

Provenance & Evidence