Potassium Carbonate → 1-(4-Fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide

HRID 2368473Notes

Reaction equation

HRID 2368473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][N:10]=[C:9]2[SH:19])=[CH:4][CH:3]=1.[F:20][C:21]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:22]=1[CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][N:10]=[C:9]2[S:19][CH2:23][C:22]2[C:25]([F:30])=[CH:26][CH:27]=[C:28]([F:29])[C:21]=2[F:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5190612,3,6-Trifluorobenzyl bromideHCID 178502684HCID 178502684, compound

Product 1

HCID 866775411-(4-Fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide (8) (153 mg, 0.54 mmol), 2,3,6-trifluorobenzyl bromide (71 μL, 0.54 mmol), and potassium carbonate (90 mg, 0.65 mmol) in acetone (5 mL) was heated at reflux for 3 h. The reaction was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-N-methoxy-N-methyl-2-((2,3,6-trifluorobenzyl)thio)-1H-imidazole-5-carboxamide (9) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3abee8ec02414b188d5f411d601a442d
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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