Nitrogen → HCID 118006351, compound

HRID 926519Notes

Reaction equation

HRID 926519 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])[C:17]([CH3:20])=[N:16][CH:15]=3)[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]([F:30])=[CH:26][CH:25]=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[N:18]([CH3:19])[C:17]([CH3:20])=[N:16][CH:15]=3)=[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]([F:30])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 118006373HCID 118006373, compound

Product 1

HCID 118006351HCID 118006351, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (224.2 mg, 0.526 mmol, Intermediate 46: step a), 1,4-dioxane (2.6 mL) and activated MnO2 (232 mg, 2.67 mmol) were combined in a round-bottom flask and the mixture was refluxed under a positive pressure of N2 overnight. 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 provide 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-8fa0ded9e2ef423791d66bb4777ac496
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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