反应详情

温度

80 °C

[(S)-4-(3-Allyloxy-pyridin-2-ylmethyl)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid isopropyl ester (40 g, 87.3 mmol) and 1,4-dioxane (400 mL) are combined and the mixture degassed by bubbling in nitrogen for one hour. Then triethylamine (24.4 mL, 174.7 mmol) and formic acid (6.60 mL, 174.7) are added and the mixture heated under nitrogen at 80° C. Tetrakis(triphenylphosphine)palladium (1.02 g, 0.87 mmol) is added while maintaining the nitrogen atmosphere. The reaction is heated at 80° C. for 3 h and then cooled to room temperature. The reaction is filtered through a pad of diatomaceous earth. The filtrate is evaporated and the crude material dried under vacuum to afford a brown solid. The solid is dissolved in NMP (100 mL) and then added to water (1.2 L). A pale cream solid is collected by filtration and dried overnight under vacuum to afford 41 g of crude material. The material is purified by recrystallization from acetonitrile and then dried under vacuum to constant weight to afford the title compound (29.5 g, 86%). LC-ES/MS m/z: 391.1 [M+H]+.

1. customthe mixture degassed
2. customby bubbling in nitrogen for one hour
3. temperaturewhile maintaining the nitrogen atmosphere
4. temperatureThe reaction is heated at 80° C. for 3 h
5. temperaturecooled to room temperature
6. filtrationThe reaction is filtered through a pad of diatomaceous earth
7. customThe filtrate is evaporated
8. dry with materialthe crude material dried under vacuum
9. customto afford a brown solid
10. filtrationA pale cream solid is collected by filtration
11. customdried overnight under vacuum
12. customto afford 41 g of crude material
13. customThe material is purified by recrystallization from acetonitrile
14. customdried under vacuum to constant weight