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

HRID 388680ノート

反応式

HRID 388680 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9f1d22f4421e4d049dc54b5896c7bf95
出典データセット
uspto-grants-2013_02
特許番号
US08377962B2

反応ノート

読み込み中…