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

HRID 1639819
ノート
印刷プレビュー

反応式

HRID 1639819 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-12ae5e7c1a5c4298803e459f8112c0dd
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110585B2

反応ノート

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