Water → 1-Benzyl-1H-indole-5-carbonitrile

HRID 1361030ノート

反応式

HRID 1361030 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

生成物 1

HCID 161146831-Benzyl-1H-indole-5-carbonitrile収率 98.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Cyanoindole (1.0 g, 7.0 mmol) was dissolved in N,N-dimethylformamide (14 mL) and cooled in an ice-water bath. Sodium hydride (0.31 g, 60%, 7.8 mmol) was added, and the resulting suspension was stirred for 30 min. Benzyl chloride (0.85 mL, 0.94 g, 7.4 mmol) was added, and the cooling was discontinued. The stirring was continued for 65 hours at room temperature. Water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were washed with brine (30 mL) and dried with sodium sulfate (1 hour). Filtration and concentration yielded the crude material. Purification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3 afforded 1.60 g 1-benzyl-1H-indole-5-carbonitrile.

後処理

  1. temperaturecooled in an ice-water bath
  2. waitThe stirring was continued for 65 hours at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic phases were washed with brine (30 mL)
  5. dry with materialdried with sodium sulfate (1 hour)
  6. filtrationFiltration and concentration
  7. customyielded the crude material
  8. customPurification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3

出典と根拠

ORDレコード
ord-64f854cb2e3e4171a602c7cf64ebaf36
出典データセット
uspto-grants-2011_02
特許番号
US07879893B2

反応ノート

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