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Water → ethyl (2E)-3-(2-methylimidazo[1,2-a]pyridin-5-yl)acrylate

HRID 1639819
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HRID 1639819 반응식
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH3:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.O.O.O.C([O-])(=O)C.[Na+].[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].O>CN(C)C(=O)C>[CH3:11][C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2](/[CH:22]=[CH:21]/[C:20]([O:24][CH2:25][CH3:26])=[O:23])[N:7]2[CH:8]=1
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6

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HCID 962WaterHCID 8821Ethyl AcrylateHCID 126377285-Bromo-2-methylimidazo[1,2-a]pyridineHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 66720685ethyl (2E)-3-(2-methylimidazo[1,2-a]pyridin-5-yl)acrylate수율 55%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
100 °C

실험 절차

To a solution of 5-bromo-2-methylimidazo[1,2-a]pyridine (5.00 g, 23.7 mmol) in N,N-dimethylacetamide (60 mL) were added sodium acetate trihydrate (3.89 g, 47.4 mmol), ethyl acrylate (3.10 mL, 28.4 mmol) and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (1.73 g, 2.37 mmol) at room temperature, and the mixture was stirred under nitrogen stream at 100° C. for 24 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (3.00 g, yield 55%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

출처 및 근거

ORD 기록
ord-12ae5e7c1a5c4298803e459f8112c0dd
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08110585B2

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