Water → HCID 51347934, compound

Participants

Reaction Conditions

Reaction Steps

2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-methoxyphenyl)-1H-indole-1-carboxamide (8 mg, 0.02 mmol) was dissolved in 8 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.40 ml) was added drop wise and the mixture was stirred at 0-2° C. for 16 h. A few drops MeOH were added followed by water. The layers were separated and the organic layer was concentrated. The crude product was purified by preparative HPLC. 3.4 mg 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide was obtained. ES/MS m/z: 376.1 (pos. M+H), 374.2 (neg. M−H); 1H NMR (acetone-d6, 500 MHz): 7.90 (m, 1H), 7.63 (m, 1H), 7.33 (m, 1H), 7.23 (m, 1H), 7.14 (m, 2H), 6.88 (m, 2H), 3.38 (m, 2H), 2.04 (s, 3H), 2.03 (s, 3H) and 1.16 (t, 3H, J=7.3 Hz).

Provenance & Evidence