Triisopropylsilyl chloride → HCID 57830996, 화합물

HRID 1642070노트

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HRID 1642070 반응식
[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1

참가 물질

5

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HCID 139400Triisopropylsilyl chlorideHCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

생성물 1

HCID 57830996HCID 57830996, 화합물수율 95%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of the 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine from the previous step in 30 mL of tetrahydrofuran stirring at 0° C. under argon atmosphere was treated with lithium hexamethyldisilylazide (6 mL, 1 M in hexanes, 6 mmol), followed by triisopropylsilyl chloride (1.1 mL, 5.2 mmol). After 30 m at 0° C., the solution was warmed to ambient temperature and diluted with 20% ethyl acetate in hexanes, then washed twice with water and once with brine. After drying the organic layer over magnesium sulfate, filtration was followed by solvent removal and flash chromatography of the resultant residue using 2.5% ethyl acetate in hexanes, to furnish 2-Chloro-7-iodo-5-triisopropylsilanyl-5H-pyrrolo[2,3-b]pyrazine (1.68 g, 95% over two steps).

후처리

  1. washwashed twice with water and once with brine
  2. customAfter drying the organic layer
  3. filtrationover magnesium sulfate, filtration
  4. customwas followed by solvent removal and flash chromatography of the resultant residue

출처 및 근거

ORD 기록
ord-4bb39287e5954cb5ba01a03605858fe1
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119636B2

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