Ammonium formate → 4-hydroxy-7-methoxy-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline

HRID 420067노트

반응식

HRID 420067 반응식
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:23]CC3C=CC(OC)=CC=3)=[CH:8][C:9]([N:14]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15]3)=[N:10]2)=[CH:5][CH:4]=1.C([O-])=O.[NH4+]>CCO.[Pd]>[OH:23][C:7]1[C:6]2[C:11](=[C:12]([CH3:13])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[C:9]([N:14]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15]2)[CH:8]=1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 566051607-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline

생성물 1

HCID 1784877104-hydroxy-7-methoxy-8-methyl-2-(3-trifluoromethyl-1H-pyrazol-1-yl)-quinoline수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of compound 87c (885 mg, 1.99 mmol), ammonium formate (629 mg, 9.98 mmol), and Pd/C (89 mg, 10% w) in EtOH (16 mL) was refluxed for 1 hr. The reaction was then filtered though celite and concentrated under reduced pressure. The residue was diluted with DCM and washed with water. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (petroleum ether/EtOAc) to yield compound 88c as a white solid in 93% yield.

후처리

  1. temperaturewas refluxed for 1 hr
  2. filtrationThe reaction was then filtered though celite and
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with DCM
  5. washwashed with water
  6. dry with materialOrganics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified by chromatography on silica gel (petroleum ether/EtOAc)

출처 및 근거

ORD 기록
ord-a79e8277c9be414daee38cf98f0b6688
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093379B2

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