Potassium Carbonate → 2-Chloro-5-((5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzonitrile

HRID 1627252Notes

Reaction equation

HRID 1627252 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:16](=[S:25])[NH:15][CH:14]=2)([CH3:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([Cl:42])=[C:38]([CH:41]=1)[C:39]#[N:40]>CC(C)=O>[Cl:42][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][S:25][C:16]2[N:17]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[C:13]([C:10]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=3)([CH3:12])[CH3:11])=[CH:14][N:15]=2)=[CH:41][C:38]=1[C:39]#[N:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140330355-(Bromomethyl)-2-chlorobenzonitrileHCID 667409645-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione

Product 1

HCID 667403762-Chloro-5-((5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzonitrileYield 60.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-(2-(3-chloro-4-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (125 mg, 0.33 mmol) in acetone (2 mL) were added K2CO3 (70, mg, 0.50 mmol) and 5-(bromomethyl)-2-chlorobenzonitrile (92 mg, 0.40 mmol). The mixture was stirred at room temperature for 2 h and filtered. The mother liquor was concentrated and purified by column chromatography (silica, 0 to 30% EtOAc/Hex) to afford the title compound (105 mg, 60%) as a white solid. MS (EI) m/z 526 (MH+).

Workup

  1. filtrationfiltered
  2. concentrationThe mother liquor was concentrated
  3. custompurified by column chromatography (silica, 0 to 30% EtOAc/Hex)

Sources & evidence

ORD record
ord-7c28c9b98b314b70a13535e2678195a8
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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