p-Toluenesulphonyl cyanide → 3-(Isoquinolin-6-yl)propiolonitrile

HRID 598841노트

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HRID 598841 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[CH:6]2)#[CH:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.S([C:33]#[N:34])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[CH:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[C:2][C:33]#[N:34])=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]=1

참가 물질

5

반응물 3

HCID 87946p-Toluenesulphonyl cyanideHCID 2733832Lithium HexamethyldisilazideHCID 579505416-Ethynylisoquinoline

생성물 1

HCID 579506673-(Isoquinolin-6-yl)propiolonitrile수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 6-ethynylisoquinoline (0.10 g, 0.65 mmol) in 6.5 mL of THF at −78° C. was added LiHMDS, (0.78 mL, 1.0 M in THF). After 5 minutes, the mixture was warmed to 0° C. The mixture was stirred for 30 minutes and then chilled to −78° C. Tosyl cyanide (0.18 g, 0.98 mmol) was added. After 5 minutes, the reaction was warmed to 0° C. and stirred for 1 hour. The reaction was quenched with 10 mL of aq. NH4Cl. The biphasic mixture was extracted twice with 10 mL of EtOAc and the combined organic extracts were washed with 15 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 20% EtOAc/hexanes) afforded 3-(isoquinolin-6-yl)propiolonitrile (0.065 g, 0.36 mmol, 56% yield) as a white solid.

후처리

  1. temperaturechilled to −78° C
  2. waitAfter 5 minutes
  3. temperaturethe reaction was warmed to 0° C.
  4. stirringstirred for 1 hour
  5. customThe reaction was quenched with 10 mL of aq. NH4Cl
  6. extractionThe biphasic mixture was extracted twice with 10 mL of EtOAc
  7. washthe combined organic extracts were washed with 15 mL of brine
  8. dry with materialdried over MgSO4
  9. filtrationFiltration and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-245ca8ef74164bcc8a57141d485ba1d4
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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