(3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoate → (2,6-Difluoropyridin-4-yl)methyl benzoate

HRID 426299노트

반응식

HRID 426299 반응식
[C:1]([O:9][CH2:10][C:11]1[C:16](Cl)=[C:15]([F:18])[N:14]=[C:13]([F:19])[C:12]=1Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[C:1]([O:9][CH2:10][C:11]1[CH:16]=[C:15]([F:18])[N:14]=[C:13]([F:19])[CH:12]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 59184839(3,5-Dichloro-2,6-difluoropyridin-4-yl)methyl benzoate

생성물 1

HCID 59184643(2,6-Difluoropyridin-4-yl)methyl benzoate수율 61%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

(3,5-dichloro-2,6-difluoropyridin-4-yl)methyl benzoate (19.6 g, 61.6 mmol), anhydrous ethanol (150 ml), and 10% palladium on carbon (3 g) were placed into a 500 mL bottle. The mixture was hydrogenated under hydrogen atmosphere (50 psi) for 1.5 hr. The reaction mixture was filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4)) to afford 9.15 g (61%) of (2,6-difluoropyridin-4-yl)methyl benzoate as a white solid. m.p. 83-84° C. 1H NMR (200 MHz, CDCl3) δ 5.42 (2H, s), 6.87 (2H, s), 7.45-7.67 (3H, m), 8.08-8.13 (2H, m).

후처리

  1. customfor 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:4))

출처 및 근거

ORD 기록
ord-ebf77b56b0364d1491516879aa57c246
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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