(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 526843Notes

Reaction equation

HRID 526843 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:14]3[N:18]([CH3:19])[N:17]=[N:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:20][CH3:21])[C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1>[O-2].[O-2].[Mn+4].O1CCOCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[N:18]([CH3:19])[N:17]=[N:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:20][CH3:21])[C:3]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 86715635(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 86715636(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

To a flask containing (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (745 mg, 1.61 mmol, Intermediate 9: step a) was added 1,4-dioxane (35 mL), producing a suspension at room temperature. Warming to 45° C. formed a homogeneous solution. Then manganese dioxide (719 mg, 8.28 mmol) was introduced and the mixture was heated to 85° C. After 2 hours, the contents were filtered through Celite® while still warm and rinsed with THF. The solution was concentrated and the crude material was triturated with Et2O to provide the title compound as a bright white solid. The mother liquors were re-purified by concentrating and re-triturating with Et2O to afford additional title compound.

Workup

  1. customproducing a suspension at room temperature
  2. customformed a homogeneous solution
  3. temperaturethe mixture was heated to 85° C
  4. filtrationthe contents were filtered through Celite®
  5. temperaturewhile still warm
  6. washrinsed with THF
  7. concentrationThe solution was concentrated
  8. customthe crude material was triturated with Et2O

Sources & evidence

ORD record
ord-e038ea1e6c3047d7a5ad152e58eb8ce2
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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