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Water → 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde

HRID 1932399
ノート
印刷プレビュー

反応式

HRID 1932399 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([C:32]#N)[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12.[OH2:34].[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([CH:32]=[O:34])[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 67141782HCID 67141782、化合物

生成物 1

HCID 866152637-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde収率 16%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Diisobutyl aluminum hydride (1.0M in toluene solution; 1.98 ml, 1.98 mmol) was added at −78° C. to a solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 099 mmol) prepared in Example 682 in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred for 5 hours and then diluted with diethyl ether. Water (2 ml) and 15% sodium hydroxide solution (2 ml) were added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 50.6 mg of the titled compound as a white solid. (Yield: 16%).

後処理

  1. stirringwas then stirred for 30 minutes
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

出典と根拠

ORDレコード
ord-7dbb6da45a164d0aa59ed777b1cd8430
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188114B2

反応ノート

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