HCID 86716092, compound → HCID 86716093, compound

HRID 627527Notes

Reaction equation

HRID 627527 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[C:5]([CH3:27])[CH:6]=[C:7]([CH:19]([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1>ClCCCl.C(Cl)Cl.CO.O=[Mn]=O>[Cl:1][C:2]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([Cl:18])[C:9]2[C:4](=[C:5]([CH3:27])[CH:6]=[C:7]([C:19]([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)=[O:20])[CH:8]=2)[N:3]=1

Participants

5

Reactant 1

HCID 86716092HCID 86716092, compound

Product 1

HCID 86716093HCID 86716093, compound

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 111,2-DichloroethaneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of crude (2,4-dichloro-8-methyl-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol (801 mg, assume 1.46 mmol, Intermediate 48, step a) in DCE (15 mL) was stirred at 70° C. until a milky mixture resulted with no visible particulates. This was cooled to room temperature and treated with MnO2 (1.27 g, 14.5 mmol), and stirred under air (capped) at 70° C. for 35 hours. The reaction was diluted with 9:1 DCM/MeOH (10 mL) and Celite®, filtered on a bed of Celite®, and concentrated to provide an oil. This was flash chromatographed with a DCM to 100% EtOAc gradient to afford the title compound as a white foam.

Workup

  1. customresulted with no visible particulates
  2. temperatureThis was cooled to room temperature
  3. stirringstirred under air (capped) at 70° C. for 35 hours
  4. filtrationfiltered on a bed of Celite®
  5. concentrationconcentrated
  6. customto provide an oil
  7. customThis was flash chromatographed with a DCM to 100% EtOAc gradient

Sources & evidence

ORD record
ord-dee682c12de142deac8d009cc5f79891
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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