Nitrogen → (4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone

HRID 926521Notes

Reaction equation

HRID 926521 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:14]3[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:22][CH3:23])[C:3]=1[CH2:24][C:25]1[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=1.N#N>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[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:22][CH3:23])[C:3]=1[CH2:24][C:25]1[CH:26]=[N:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 118006074(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol

Product 1

HCID 118006248(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol (810 mg, 1.66 mmol, Intermediate 47: step a), 1,4-dioxane (8.5 mL) and activated MnO2 (724.4 mg, 8.332 mmol) were combined in a round-bottom flask and the mixture was heated to reflux under a positive pressure of N2. After 4 hours, the reaction was cooled to room temperature and filtered through Celite®, rinsing with dichloromethane. The filtrate was washed with water, and the aqueous layer was extracted with additional dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness to provide the title compound which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. filtrationfiltered through Celite®
  3. washrinsing with dichloromethane
  4. washThe filtrate was washed with water
  5. extractionthe aqueous layer was extracted with additional dichloromethane
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a05dfad75e584505ab1ac0743e9f859e
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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