反应详情

Sodium hydride (275 mg, 11.45 mmol) was washed with hexane and dried under vacuum. DMF (4 mL) was added, resulting in a suspension. 2,3,4,5-Tetrahydro-2-methyl-8-chloro-1H-pyrido[4,3-b]indole (500 mg, 2.27 mmol) dissolved in DMF (2 mL) was added dropwise and the reaction mixture stirred for 30 min at RT. 4-(2-Methyl-oxiranyl)-pyrimidine (620 mg, 4.55 mmol) dissolved in DMF (2 mL) was added dropwise and the reaction mixture was stirred overnight at RT. The progress of reaction was monitored by TLC. The mixture was quenched with ice-cold water and the mixture extracted with EtOAc (3×30 mL). The combined organic layer was washed with water (4×20 mL) followed by brine (1×20 mL), dried over sodium sulfate and the solvent evaporated under vacuum. The residue was washed with hexane and crystallized from ether: DCM and hexane. 1HNMR (CD3OD, Oxalate salt) d (ppm): 9.10 (s, 1H), 8.50 (d, 1H), 7.50 (d, 1H), 7.36 (s, 1H), 7.10 (d, 1H), 6.95 (d, 1H), 4.40 (m, 4H), 3.60 (m, 2H), 3.40 (m, 1H), 3.20 (m, 1H), 3.05 (s, 3H), 1.60 (s, 3H).

1. customdried under vacuum
2. additionDMF (4 mL) was added
3. customresulting in a suspension
4. additionwas added dropwise
5. additionwas added dropwise
6. stirringthe reaction mixture was stirred overnight at RT
7. customThe progress of reaction
8. customThe mixture was quenched with ice-cold water
9. extractionthe mixture extracted with EtOAc (3×30 mL)
10. washThe combined organic layer was washed with water (4×20 mL)
11. dry with materialdried over sodium sulfate
12. customthe solvent evaporated under vacuum
13. washThe residue was washed with hexane
14. customcrystallized from ether