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

HRID 925961Notes

Reaction equation

HRID 925961 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ff5f7410a5784fde8c30786c36a69628
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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