Azidotrimethylsilane → 3-Chloro-6-(2H-1,2,3-triazol-4-yl)isoquinoline

HRID 523062노트

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HRID 523062 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[CH:13])=[CH:7][CH:6]=2.[N:14]([Si](C)(C)C)=[N+:15]=[N-:16]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:13]=[N:16][NH:15][N:14]=1)=[CH:7][CH:6]=2

참가 물질

5

반응물 2

HCID 78378AzidotrimethylsilaneHCID 899955703-Chloro-6-ethynylisoquinoline

생성물 1

HCID 899956273-Chloro-6-(2H-1,2,3-triazol-4-yl)isoquinoline수율 61%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

3-chloro-6-ethynylisoquinoline (Preparation 50, 120 mg, 0.64 mmol) was dissolved in dry DMF (1 mL). Azidotrimethylsilane (1 mL, 7.5 mmol) was added and the reaction stirred at 120° C. for 2 hours. The reaction was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 2% 7N NH3 in methanol in DCM followed by elution through an SCX-2 column using 50% methanol in chloroform followed by 50% 7N NH3 in methanol in chloroform to afford the title compound as a pale brown powder (90 mg, 61%).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washThe organic solution was washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 2% 7N NH3 in methanol in DCM
  7. washfollowed by elution through an SCX-2 column

출처 및 근거

ORD 기록
ord-c19af088cac24e75b2d62f82f2dc7351
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334286B2

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