Ethanol → Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

HRID 600637

반응식

HRID 600637 반응식
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(O)C>COCCOC>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:8]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 5743468N5,N5-Dimethylpyridine-2,5-diamine

생성물 1

HCID 44124134Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
20 °C

실험 절차

To a suspension of 0.2 g of 5-dimethylaminopyridine-2-amine in 3 mL of DME are added 215 μL of ethyl bromopyruvate. The reaction mixture is stirred at 20° C. for 16 hours and then, after addition of 3 mL of ethanol, for 16 hours at reflux, and finally concentrated under reduced pressure. The residue is filtered on a cartridge of 15 g of silica, eluting with a mixture of dichloromethane and methanol (98/2). The fractions containing the expected product are combined and washed with saturated sodium bicarbonate solution. The organic phase is dried and concentrated to dryness under reduced pressure to give 76 mg of ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate in the form of a green oil, which is used without further purification in the rest of the synthesis.

후처리

  1. temperaturefor 16 hours at reflux
  2. concentrationfinally concentrated under reduced pressure
  3. filtrationThe residue is filtered on a cartridge of 15 g of silica
  4. washeluting with a mixture of dichloromethane and methanol (98/2)
  5. additionThe fractions containing the expected product
  6. washwashed with saturated sodium bicarbonate solution
  7. customThe organic phase is dried
  8. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-b32fd19204cd4b839ca6f5a53c41e8d4
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902219B2

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