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Sodium hydride → 3-[4-(2-cyano-2-phenylethyl)phenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2255572
ノート
印刷プレビュー

反応式

HRID 2255572 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.[H-].[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:26]#[N:27])=[CH:20][CH:19]=1>CN(C=O)C>[C:26]([CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]=[C:9]2[CH2:11][CH2:12][CH3:13])=[CH:19][CH:20]=1)#[N:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineHCID 193855943-[4-(Bromomethyl)phenyl]2-phenylpropanonitrile

生成物 1

HCID 197381193-[4-(2-cyano-2-phenylethyl)phenyl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine収率 19.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 7-methyl-2-propylimidazo [4,5-b]pyridine (106 mg, 0.61 mmol) in DMF (3 mL) was added NaH (0.91 mmol). The suspension was stirred at room temperature for 30 minutes, at which time a solution of the product of Step D (200 mg, 0.667 mmol) in DMF (2 mL) was added. The mixture was stirred for 2 hours at room temperature, quenched with water, and then concentrated in vacuo. The residue was partitioned between water and EtOAc, and the combined organic layers were washed with brine, dried (K2CO3), filtered, and evaporated in vacuo. The residue was chromatographed on a silica gel flash chromatography column eluted with 50% ethyl acetate/hexane to afford 46 mg (19%) of the title compound.

後処理

  1. additionwas added
  2. customquenched with water
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on a silica gel flash chromatography column
  10. washeluted with 50% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-acaff30b281d49a4b8e62b363b4d0008
出典データセット
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05240938

反応ノート

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