Triethylamine → HCID 58378199, compound

Participants

Reaction Steps

Under nitrogen atmosphere, a solution of 2-(3,5-dimethyl-isoxazol-4-yl)-1-(4-hydroxy-phenyl)-1H-indole-3-carbonitrile (Example 51), 12 eq hydroxylamine hydrochloride and 12 eq triethylamine in EtOH was heated at 100° C. for 24 hours. The reaction mixture was cooled to rt, diluted with methanol, precipitation filtered off and subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by 1H-NMR and LC/MS. Purity was determined by analytical HPLC. ES/MS m/z: 363.5 (M+H), 361.6 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.14-8.13 (s, OH), 8.08-8.04 (m, 1H), 7.23-7.14 (m, 3H), 7.15-7.06 (m, 2H), 6.96-6.91 (m, 2H), 5.18-5.07 (m, 2H), 2.16 (s, 3H), 2.00 (s, 3H).

Provenance & Evidence