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

HRID 1361030노트

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HRID 1361030 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 161146831-Benzyl-1H-indole-5-carbonitrile수율 98.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64f854cb2e3e4171a602c7cf64ebaf36
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879893B2

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