Aluminum → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone

HRID 928802Notes

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]([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[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]([C:30]([F:32])([F:31])[F:33])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a 100 mL flask containing (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol (1.68 g, 3.53 mmol, Intermediate 49: step a) was added 1,4-dioxane (85 mL) to give a suspension at room temperature. Heating to approximately 45° C. formed a clear homogeneous solution. Then activated MnO2 (1.5 g, 17.2 mmol) was introduced and the mixture was heated to reflux in an aluminum heating mantle under an atmosphere of N2. After 70 minutes, the contents were cooled to 60° C. and then filtered through a Celite® pad and rinsed with THF. The resulting solution was concentrated and passed through a silica gel column (5% MeOH-DCM) to give the title compound as a white powder.

Workup

customto give a suspension at room temperature
customformed a clear homogeneous solution
temperaturethe mixture was heated
temperaturethe contents were cooled to 60° C.
filtrationfiltered through a Celite® pad
washrinsed with THF
concentrationThe resulting solution was concentrated

Sources & evidence

ORD record: ord-0cb78894e72843d28dd2470697242b43
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290476B2

Reaction notes

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