Sodium Iodide → (4-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)phenyl)acetonitrile

HRID 2206014ノート

反応式

HRID 2206014 の反応式
C[O:2][C:3]1[C:8]2[C:9]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=3)=[CH:10][N:11]([CH:12]([CH2:16][CH3:17])[CH2:13][O:14][CH3:15])[C:7]=2[CH:6]=[CH:5][N:4]=1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:15][O:14][CH2:13][CH:12]([N:11]1[C:7]2[CH:6]=[CH:5][NH:4][C:3](=[O:2])[C:8]=2[C:9]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][C:25]#[N:26])=[CH:22][CH:23]=2)=[CH:10]1)[CH2:16][CH3:17]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 117988143(4-(4-methoxy-1-(1-methoxybutan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl)phenyl)acetonitrile

生成物 1

HCID 117988077(4-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)phenyl)acetonitrile収率 67.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of (4-(4-methoxy-1-(1-methoxybutan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl)phenyl)acetonitrile (18.0 mg) in acetonitrile (2 mL) were added sodium iodide (19.3 mg) and chloro(trimethyl)silane (0.065 mL), and the mixture was stirred overnight at 50° C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (11.6 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-4e26cce00f4c460ca6a9302fb547cab1
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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