Potassium Carbonate → 2-(4-bromo-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 83915Notes

Reaction equation

HRID 83915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([SH:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].C([O-])([O-])=O.[K+].[K+].[Br:32][C:33]1[CH:34]=[C:35]([F:42])[C:36]([CH2:40]Br)=[C:37]([F:39])[CH:38]=1>CC(C)=O>[Br:32][C:33]1[CH:34]=[C:35]([F:42])[C:36]([CH2:40][S:23][C:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:24][CH3:25])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[C:37]([F:39])[CH:38]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27733055-Bromo-2-(bromomethyl)-1,3-difluorobenzeneHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

Product 1

HCID 667405782-(4-bromo-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazoleYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (1.00 g, 2.65 mmol) and K2CO3(0.51 g, 3.70 mmol) in acetone (13 mL) was added 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (0.91 g, 3.18 mmol). The reaction mixture was stirred 1 h and then filtered. The filtrate was concentrated under reduced pressure and purified by chromatography (10% MeOH/DCM) to yield 2-(4-bromo-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole as a tan solid (1.34 g, 87%). MS (EI) m/z 581 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-ea2c88602b3a4808999af6ef1b22641f
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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