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

HRID 233740

反応式

HRID 233740 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a4e113514aa465c8b69e6ddfbb6fcf7
出典データセット
uspto-grants-1997_01
特許番号
US05594010

関連ノート

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