Potassium Carbonate → 2-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl ester

HRID 571684노트

반응식

HRID 571684 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([F:24])([F:23])C([O-])=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH:19]([F:24])[F:23])=[CH:7][N:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 178498852HCID 178498852, 화합물

생성물 1

HCID 578272862-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl ester수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluoroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100° C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methyl-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

후처리

  1. customThe reaction vessel was capped
  2. temperaturecooled to room temperature
  3. filtrationThe reaction was filtered
  4. washwashing with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. washwashed with brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (0-40% EtOAc/hex)

출처 및 근거

ORD 기록
ord-54a46a51e9eb40d1978da4ca3d3e3373
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029362B2

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