Dimethylformamide → 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2196470Notes

Reaction equation

HRID 2196470 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[NH:19][CH:20]=1)=[O:15])[CH3:12].CN(C=O)C>CCOC(C)=O>[CH2:11]([O:13][C:14]([C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)[N:19]([CH2:8][CH2:9][CH3:10])[CH:20]=1)=[O:15])[CH3:12].[CH2:11]([O:13][C:14]([C:16]1[N:17]([CH2:8][CH2:9][CH3:10])[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Br:28])=[CH:26][CH:27]=2)=[N:19][CH:20]=1)=[O:15])[CH3:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 178469892HCID 178469892, compound

Product 2

HCID 580889072-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl esterYield 33.6%HCID 672311902-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl esterYield 20%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (2.6 g, 18.7 mmol) and 1-iodopropane (669.7 μL, 6.9 mmol) were added to 2-(4-Bromobenzyl)-1H-imidazole-4-carboxylic acid ethyl ester (1.9 g, 6.2 mmol) dissolved in DMF (40 mL, 500 mmol). The mixture was heated at 60° C. for 5 hours. The mixture was cooled and then diluted with EtOAc (100 mL), washed with water and saturated aqueous NaCl (100 mL each), dried over MgSO4, filtered and concentrated. The mixture was purified by column chromatography (20-60% EtOAc in Hexanes) to yield the desired product, 2-(4-bromobenzyl)-1-propyl-1H-imidazole-4-carboxylic acid ethyl ester (736 mg, 33.6% yield), and its regioisomer, 2-(4-bromobenzyl)-3-propyl-3H-imidazole-4-carboxylic acid ethyl ester (500 mg, 20% yield). The structures were confirmed by NMR.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water and saturated aqueous NaCl (100 mL each)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by column chromatography (20-60% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-419f44c7f1b54860bd36f60bffb90287
Source dataset
uspto-grants-2012_12
Patent number
US08338418B2

Reaction notes

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