Methyl iodide → 5-Bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 545361Notes

Reaction equation

HRID 545361 reaction equation
[Br:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[C:19]([OH:21])=[O:20].[C:22](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:22][O:20][C:19]([C:3]1[N:4]([CH3:18])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)=[N:6][C:2]=1[Br:1])=[O:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 671331915-bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

Product 1

HCID 671331955-Bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl esterYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.826 g (5.0 mmol) of 5-bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid (example 72) in 20 ml of DMF was treated at RT with 2.073 g (15.0 mmol) of potassium carbonate, followed by addition of 0.62 ml=1.42 g (10.0 mmol) of iodomethane. After 70 hours, the reaction mixture was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane/CH2Cl2 1:0 to 0:1) to give 1.77 g (93%) of the title compound as light yellow oil. MS: 379.0 (MH+, 1Br).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with Et2O
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (n-heptane/CH2Cl2 1:0 to 0:1)

Sources & evidence

ORD record
ord-75253d57e8b447a4bbb2e12f21408ff9
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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