Pyridine → HCID 86669035, compound

Participants

Reaction Steps

2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbaldehyde (18 mg, 0.05 mmol) was dissolved in 5 ml MeOH. 5 eq hydroxylamine hydrochloride and 6 eq pyridine were added. The mixture was heated at reflux for 1.5 h and then allowed to cool to rt. 50 ml EtOAc were added, the resulting mixture was washed with brine 3× and then dried over Na2SO4. The solvent was concentrated and the crude product was purified using preparative HPLC. 3.5 mg 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbaldehyde oxime was obtained. The title compound was identified by 1H-NMR which showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained. ES/MS m/z: 348.01 (M+H), 346.18 (M−H); 1H NMR (MeOD, 500 MHz): 8.38 (s, 1H), 8.26 (m, 1H), 7.66 (m, 1H), 7.35 (m, 1H), 7.25 (m, 1H), 7.11 (m, 2H), 6.80 (m, 2H), 2.13 (s, 3H) and 1.99 (s, 3H).

Provenance & Evidence