Ethyl Acetate → 3-Pyridinol, 6-amino-2-(trifluoromethyl)-

HRID 1049343노트

반응식

HRID 1049343 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([NH2:19])=[N:13][C:14]=2[C:15]([F:18])([F:17])[F:16])O1.B(O[O-])=[O:22].O.[Na+].CCOC(C)=O>C1COCC1.O>[NH2:19][C:12]1[N:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]([OH:22])=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 23695970Perboric acid, sodium salt, monohydrateHCID 904024785-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine

생성물 1

HCID 904033283-Pyridinol, 6-amino-2-(trifluoromethyl)-수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine (0.598 g, 2.076 mmol) in THF (10 mL) and water (10 mL) was treated with sodium perborate monohydrate (0.332 g, 3.32 mmol) and stirred at RT overnight. The mixture was treated with EtOAc and the solids removed via filtration through diatomaceous earth. The filtrate was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 6-amino-2-(trifluoromethyl)pyridin-3-ol (92 mg, 25%). 1H NMR (400 MHz, DMSO-d6): δ 9.47 (s, 1H), 7.15 (d, J=8.9 Hz, 1H), 6.58 (d, J=8.9 Hz, 1H), 5.70 (s, 2H); MS (ESI) m/z: 179.1 (M+H+).

후처리

  1. customthe solids removed via filtration through diatomaceous earth
  2. additionThe filtrate was treated with brine
  3. extractionextracted with EtOAc (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

출처 및 근거

ORD 기록
ord-d78c7901059e48ef842d85d76c2c542d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382228B2

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