Indole → HCID 725887, compound

Participants

Reaction Steps

A solution of potassium tert-butoxide (0.25 mmol) in TBF (0.25 mL) was added to a solution of 1H-indole (30 mg, 0.25 mmol) in a mixture of dioxane (6 m]L) and DMF (1.5 mL) under argon atmosphere at ambient temperature. The solution was stirred for 5 min before a solution of 2-bromo-N-(3-trifluoromethyl-phenyl)-acetamide (0.2 mmol) in DMF (1 mL) was added dropwise. The reaction mixture was stirred overnight at ambient temperature and the solvents were-removed in vacuum. The crude product was purified on a preparative LC/MS (XTerra C8 column 19×100 mm, 0.1 M aqueous NH4Ac/CH3CN). The product-containing fractions were pooled and lyophilized to afford 24 mg (38%) of the title compound. Calculated for C17H13F3N2O m/z: 318.3, found 319.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 4.9 (s, 2H), 6.7 (d, J=3.0 Hz, 1H), 7.0 (s, 1H), 7.1 (d, J=3.0 Hz, 1H), 7.2-7.3 (m, 5 H), 7.4 (m, 1H), 7.6 (s, 1H), 7.7 (d, J=8.1 Hz, 1H).

Provenance & Evidence