反应详情

温度

65 °C

4-(2-(3,5-Dimethylisoxazol-4-yl)-3-thiocyanato-1H-indol-1-yl)phenol was dissolved in DMSO and 10 eq 2 M hydroxylamine/NaHCO3 (aq) stock solution was added. The reaction was stirred at 65° C. overnight and then diluted with H2O. A precipitation was formed after stirring for 5 min. The mixture was diluted with EtOAc and diethylether, washed with NH4Cl (aq) and phases were partitioned. Organic phase was evaporated to dryness in vacuo and subjected to purification on reverse phase preparative HPLC to provide the title compound 2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl N′-hydroxycarbamimidothioate (E32). ES/MS m/z: 395.17 (M+H), 393.19 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.88 (broad s, 1H), 8.73 (broad s, 1H), 7.80-7.78 (m, 1H), 7.29-7.24 (m, 3H), 7.18 (d, 2H), 6.95 (d, 2H), 5.11 (broad s, 2H), 2.28 (s, 3H), 2.00 (s, 3H)

1. customA precipitation
2. customwas formed
3. stirringafter stirring for 5 min
4. washwashed with NH4Cl (aq) and phases
5. customwere partitioned
6. customOrganic phase was evaporated to dryness in vacuo
7. customsubjected to purification on reverse phase preparative HPLC