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Water → N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethyl-N-2-propen-1-ylpropanamide

HRID 1943131
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HRID 1943131 반응식
[Br:1][C:2]1[C:3]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[H-].[Na+].[CH2:18](I)[CH:19]=[CH2:20].O>CN(C=O)C>[Br:1][C:2]1[C:3]([N:9]([CH2:20][CH:19]=[CH2:18])[C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1
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HCID 962WaterHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 86642088N-(3-Bromo-6-chloro-2-pyridinyl)-2,2-dimethylpropanamide

생성물 1

HCID 86642089N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethyl-N-2-propen-1-ylpropanamide

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

A solution of N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethylpropanamide (2.305 g, 7.907 mmol) in DMF (40 ml) at 0° C. under argon was treated with sodium hydride (0.696 g, 17.395 mmol) and then allowed warm to rt over 0.25 h, stirred at rt for 0.25 h and then treated with allyl iodide (1.61 ml, 17.395 mmol) and stirred at rt for 1 h. The reaction was then treated with water (10 ml), concentrated to approximately 5 ml, treated with more water (200 ml) and extracted with DCM (3×200 ml). The organic extracts were dried (MgSO4), filtered, evaporated and the residue chromatographed (0-20% ethyl acetate:Hexane) to give the product as a yellow oil which solidified to an off white solid (5.324 g, 67%).

후처리

  1. stirringstirred at rt for 1 h
  2. concentrationconcentrated to approximately 5 ml
  3. additiontreated with more water (200 ml)
  4. extractionextracted with DCM (3×200 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue chromatographed (0-20% ethyl acetate:Hexane)

출처 및 근거

ORD 기록
ord-8b2175346e314c0fbc270c519cbf4919
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08389524B2

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