Aminopyrazine → 2-(Trifluoromethyl)imidazo[1,2-a]pyrazine

HRID 1454794

반응식

HRID 1454794 반응식
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]([F:15])([F:14])[F:13])=O>C(O)C>[F:13][C:12]([F:15])([F:14])[C:10]1[N:1]=[C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]2[CH:9]=1

참가 물질

4

반응물 2

HCID 78747AminopyrazineHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

생성물 1

HCID 32313062-(Trifluoromethyl)imidazo[1,2-a]pyrazine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-aminopyrazine (5.25 g, 55.2 mmol) in ethanol (120 mL) was added 1-bromo-3,3,3-trifluoroacetone (5.73 mL, 55.2 mmol). The reaction was stirred at reflux for 20 h. After evaporation of solvent, the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted three times with ethyl acetate. The combined organic phase was washed with saturated brine solution, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (silica gel, 1:1 ethyl acetate:hexane, then 100% ethyl acetate) to give the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ 8.02 (m, 2H), 8.13 (m, 1H), 9.22 (s, 1H). ESI-MS 188 (M+1).

후처리

  1. temperatureat reflux for 20 h
  2. customAfter evaporation of solvent
  3. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic phase was washed with saturated brine solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica gel, 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-c219cd9a4fc24bb98a202be7d7ca64c2
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482336B2

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