Sodium hydride → 2-Cyclopropyl-5,7-dimethyl-3-(6-bromopyridin-3-ylmethyl)imidazo[4,5-b]pyridine

HRID 233740

반응식

HRID 233740 반응식
[H-].[Na+].[CH:3]1([C:6]2[NH:7][C:8]3[C:9]([N:16]=2)=[N:10][C:11]([CH3:15])=[CH:12][C:13]=3[CH3:14])[CH2:5][CH2:4]1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][N:19]=1>CS(C)=O.O>[CH:3]1([C:6]2[N:16]([CH2:24][C:21]3[CH:20]=[N:19][C:18]([Br:17])=[CH:23][CH:22]=3)[C:9]3=[N:10][C:11]([CH3:15])=[CH:12][C:13]([CH3:14])=[C:8]3[N:7]=2)[CH2:5][CH2:4]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 64246602-Bromo-5-bromomethylpyridineHCID 103134402-Cyclopropyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine

생성물 1

HCID 152250222-Cyclopropyl-5,7-dimethyl-3-(6-bromopyridin-3-ylmethyl)imidazo[4,5-b]pyridine수율 69.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

255 mg (6.4 mmol) of sodium hydride and 994 mg (5.3 mmol) of 2-cyclopropyl-5,7-dimethylimidazo[4,5-b]pyridine are stirred at 0° C. for 2 h in 15 ml of dimethyl sulphoxide. After adding 2 g (7.97 mmol) of 2-bromo-5-bromomethylpyridine, the mixture is stirred at room temperature overnight. The reaction mixture is diluted with water and washed twice with ethyl acetate; the combined organic phases are washed with water and sodium chloride solution, dried over sodium sulphate and then chromatographed on 150 g of silica gel using ethyl acetate/petroleum ether mixtures 1:2→1:0 to yield 1.32 g of the title compound.

후처리

  1. washwashed twice with ethyl acetate
  2. washthe combined organic phases are washed with water and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customchromatographed on 150 g of silica gel

출처 및 근거

ORD 기록
ord-8a4e113514aa465c8b69e6ddfbb6fcf7
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594010

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