Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate → 1-(2-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)phenyl)-2,2-dimethyl-1-propanone

HRID 404333노트

반응식

HRID 404333 반응식
[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:11]=2[C:12]([O:14]C)=O)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:22]([Li])([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:11]=2[C:12](=[O:14])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 57467597Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 577061591-(2-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)phenyl)-2,2-dimethyl-1-propanone수율 88.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 2-(5-fluoro-2-methoxypyridin-4-yl)-5-(hydroxymethyl)benzoate T6.3 (0.307 g, 1 mmol) in THF (11 mL) at −78° C. was added tert-butyl lithium (2 mL, 3 mmol). The resulting mixture was stirred for one hour. The reaction was then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the organic solvent was removed under reduced pressure. The residue was then purified on silica gel (0-40% EtOAc in hexanes) to yield T6.4 as a colorless solid (0.28 g, 84% yield).

후처리

  1. customThe reaction was then quenched with a saturated solution of ammonium chloride
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe organic solvent was removed under reduced pressure
  6. customThe residue was then purified on silica gel (0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-04a3b4c895324c66bd092903439e2d1d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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