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

HRID 388680노트

반응식

HRID 388680 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 234c (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 236c as a white solid in 93% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 2.54 (s, 3H), 3.94 (s, 3H), 7.06 (d, J=2.48 Hz, 1H), 7.37-7.40 (m, 2H), 8.02 (d, J=9.18 Hz, 1H), 8.97 (s, 1H), 11.89 (s, 1H).

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-9f1d22f4421e4d049dc54b5896c7bf95
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377962B2

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