Water → HCID 44466355, compound

Participants

Reaction Conditions

Reaction Steps

4-(1-(4-Methoxyphenyl)-3-(methylsulfonyl)-1H-indol-2-yl)-3,5-dimethylisoxazole was dissolved in 2 ml of dry DCM and cooled to −78° C. under nitrogen. BBr3 (31 μl, 0.33 mmol) was added and the temperature was allowed to warm to RT for 2 h. Water and EtOAc were added and the phases were separated. After evaporation of the solvents, the residue was purified by preparative HPLC to provide 4-[2-(3,5-dimethyl-isoxazol-4-yl)-3-methanesulfonyl-indol-1-yl]-phenol in 27% yield. ES/MS m/z: 383.11 (M+H), 381.13 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.12 (m, 1H), 7.39-7.34 (m, 2H), 7.25-7.19 (m, 3H), 6.98 (m, 2H), 3.06 (s, 3H), 2.30 (s, 3H) and 2.09 (s, 3H).

Provenance & Evidence