反应详情

2-(3,5-Dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indole-3-carbonyl chloride was dissolved in 0.5 ml of dry MeOH and the mixture was cooled on an ice-bath. Fresh hydroxylamine was prepared by pouring a MeOH solution (0.3 ml) of hydroxylamine hydrochloride (12 mg, 0.17 mmol) into a MeOH solution (0.3 ml) of KOH (19 mg, 0.33 mmol). The mixture was filtered through a syringe filter into the cooled acid chloride solution. After 5 min, the cooling bath was removed and the reaction was allowed to warm to RT and was stirred for 10 min Water, 1M HCl and EtOAc were added and the phases were separated. After evaporation of the solvents, the residue was purified by preparative HPLC to provide methyl 2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indole-3-carboxylate in 16% yield. ES/MS m/z: 363.11 (M+H), 361.13 (M−H); 1H NMR (methanol-d4, 500 MHz): 8.21 (m, 1H), 7.32-7.26 (m, 2H), 7.20 (m, 1H), 7.13 (br s, 1H), 7.01 (br s, 1H), 6.88 (m, 2H), 3.83 (s, 3H), 2.12 (s, 3H) and 2.03 (s, 3H).

1. temperaturethe mixture was cooled on an ice-bath
2. filtrationThe mixture was filtered through a syringe
3. filtrationfilter into the cooled acid chloride solution
4. customthe cooling bath was removed
5. additionwere added
6. customthe phases were separated
7. customAfter evaporation of the solvents
8. customthe residue was purified by preparative HPLC