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

HRID 426299ノート

反応式

HRID 426299 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

(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).

後処理

  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))

出典と根拠

ORDレコード
ord-ebf77b56b0364d1491516879aa57c246
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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