Nitrogen → (4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone

HRID 926522Notes

Reaction equation

HRID 926522 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:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=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]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 118006066(4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol

Product 1

HCID 118006456(4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol (550 mg, 1.26 mmol, Intermediate 48: step a), 1,4-dioxane (6.2 mL) and activated MnO2 (551 mg, 6.34 mmol) were combined in a round-bottom flask and the mixture was refluxed under a positive pressure of N2. After 4 hours, the reaction was allowed to cool to ambient temperature, then filtered through Celite® and rinsed 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 afford the title compound which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-d7ded57607ad4d0f8f20de8f855c6560
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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