HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 928802
Notes
Print preview

Reaction equation

HRID 928802 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 5359268AluminumHCID 86715633(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol

Product 1

HCID 86715634(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst
HCID 31275
1,4-Dioxane
Solvent

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

  1. customto give a suspension at room temperature
  2. customformed a clear homogeneous solution
  3. temperaturethe mixture was heated
  4. temperaturethe contents were cooled to 60° C.
  5. filtrationfiltered through a Celite® pad
  6. washrinsed with THF
  7. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes