反应详情

To a solution of 2-methylindole-3-carboxaldehyde (10.00 g, 62.84 mmole) in MeOH (100 mL) was added 2 M CH3NH2 in MeOH (200 mL). After stirring for 3 hours at RT, the reaction solution was concentrated to a yellow oil which solidified under vacuum. This solid was dissolved in ethanol (350 mL) and NaBH4 (2.38 g, 62.8 mmole) was added. The reaction was stirred at RT for 6 hours, then was concentrated under vacuum. The remaining residue was diluted with saturated aqueous Na2CO3 (50 mL) and extracted with EtOAc (2×200 mL). The organic phase was separated, washed with brine, and dried over Na2SO4. Flash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum gave the title compound (6.88 g, 63%) as a faintly yellow viscous solid: MS (ES) m/e 175 (M+H)+.

1. concentrationthe reaction solution was concentrated to a yellow oil which
2. dissolutionThis solid was dissolved in ethanol (350 mL)
3. stirringThe reaction was stirred at RT for 6 hours
4. concentrationwas concentrated under vacuum
5. additionThe remaining residue was diluted with saturated aqueous Na2CO3 (50 mL)
6. extractionextracted with EtOAc (2×200 mL)
7. customThe organic phase was separated
8. washwashed with brine
9. dry with materialdried over Na2SO4
10. customFlash chromatography on silica gel (9:1 CHCl3/MeOH containing 5% NH4OH) and drying under high vacuum