Aluminum → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)methanone

HRID 928806Notes

Reaction equation

HRID 928806 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:14]3[O:18][C:17]([CH3:19])=[N:16][C:15]=3[CH3:20])[OH:13])[CH:10]=2)[N:5]=[C:4]([O:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.[Al]>O=[Mn]=O.O1CCOCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[O:18][C:17]([CH3:19])=[N:16][C:15]=3[CH3:20])=[O:13])[CH:10]=2)[N:5]=[C:4]([O:21][CH3:22])[C:3]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 5359268AluminumHCID 86715637(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)methanol

Product 1

HCID 86715638(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a 100 mL flask containing (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,4-dimethyloxazol-5-yl)methanol (960 mg, 2.01 mmol, Intermediate 51: step a) was added 1,4-dioxane (50 mL) and activated MnO2 (900 mg, 10.3 mmol) at room temperature. The mixture was heated to 85° C. in an aluminum heating mantle under a nitrogen atmosphere. After 60 minutes, the contents were filtered through Celite® while the solution is still warm and rinsed with THF, and concentrated to give an off white solid. The crude material was triturated with Et2O to give a white solid.

Workup

  1. filtrationthe contents were filtered through Celite® while the solution
  2. temperatureis still warm
  3. washrinsed with THF
  4. concentrationconcentrated
  5. customto give an off white solid
  6. customThe crude material was triturated with Et2O
  7. customto give a white solid

Sources & evidence

ORD record
ord-ddeb40ffb2f44b8abc1321d573f9b9bd
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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