反応 #532953

反応方程式

5-bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

DMF

NaH

NaH

iodomethane

NaH

iodomethane

iodomethane

→

title compound

5-Bromo-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

反応条件

後処理

1. 1
   温度cooled with an ice-bath
2. 2
   workup.STIRRINGthe RM was stirred for 30 min at rt
3. 3
   温度The RM was cooled with an ice-bath
4. 4
   workup.STIRRINGthe RM was stirred for 15 min at rt
5. 5
   workup.STIRRINGthe RM was stirred for 30 min at rt
6. 6
   温度The RM was cooled with an ice-bath
7. 7
   workup.STIRRINGthe RM was stirred for 15 min at rt
8. 8
   workup.STIRRINGthe RM was stirred for 1.5 h at rt
9. 9
   その他The RM was quenched with saturated aqueous NaHCO3
10. 10
    抽出extracted with EtOAc
11. 11
    洗浄The organic layer was washed with brine (3×)
12. 12
    乾燥dried over Na2SO4
13. 13
    ろ過filtered
14. 14
    その他evaporated
15. 15
    その他The residue was absorbed on silica gel
16. 16
    その他purified by flash chromatography (heptane/EtOAc 0% to 40%)
17. 17
    workup.ADDITIONThe fractions containing product
18. 18
    その他were evaporated together

実験手順

To a mixture of 5-bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (Aldrich, Buchs, Switzerland, 1.394 min) in DMF (7 ml) cooled with an ice-bath was added 55% NaH in oil (1.6 mmol) and the RM was stirred for 30 min at rt, then was added iodomethane (0.1 ml) and the RM was stirred for 30 min at rt. The RM was cooled with an ice-bath and was added 55% NaH in oil (1.6 mmol) and the RM was stirred for 15 min at rt, then was added iodomethane (0.1 ml) and the RM was stirred for 30 min at rt. The RM was cooled with an ice-bath and was added 55% NaH in oil (1.6 mmol) and the RM was stirred for 15 min at rt, then was added iodomethane (0.1 ml) and the RM was stirred for 1.5 h at rt. The RM was quenched with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine (3×), dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 40%). The fractions containing product were evaporated together to give the title compound as an off-white solid. (HPLC: tR 2.99 min (Method A); M+H=255, 257 MS-ES)

出典