Sodium Bicarbonate → Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-

HRID 715342

반응식

HRID 715342 반응식
CON(C)[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:7][CH:6]=1.[CH3:19][Mg]Br.C(=O)([O-])O.[Na+]>C1COCC1>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:8]1[N:7]=[CH:6][C:5]([C:4](=[O:17])[CH3:19])=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 86707284N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 58629124Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)nicotinamide (6.54 g, 24.8 mmol, Step-2) in THF (80 mL) is added dropwise 1.06M methylmagnesium bromide (46.7 mL, 49.5 mmol) at 0° C. The reaction mixture is stirred at rt for 1.5 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (100 mL) and extracted with EtOAc (300 mL). The organic layer is washed with water (100 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1) to give 4.51 g (83% yield) of the title compound as colorless oil.

후처리

  1. extractionextracted with EtOAc (300 mL)
  2. washThe organic layer is washed with water (100 mL×2)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1)

출처 및 근거

ORD 기록
ord-05fd2e2e06eb4df8aec4e35d9f662de3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187475B2

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