Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate

HRID 2098955노트

반응식

HRID 2098955 반응식
[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 574675964-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acid

생성물 1

HCID 57467597Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate수율 105.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
23 °C

실험 절차

To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T37.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield T37.3 as a colorless solid (0.307 g, 77% yield).

후처리

  1. concentrationThe reaction was then concentrated in vacuo
  2. additionThe reaction was diluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-740c0c42973f45e4963bc04053215a52
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450522B2

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