Water → Methyl 4'-[[4-bromo-2-butyl-5-formyl-1H-imidazol-1-yl]-methyl]-(1,1'-biphenyl)-2-carboxylate

HRID 274339Notes

Reaction equation

HRID 274339 reaction equation
[Br:1][C:2]1[NH:6][C:5]([CH2:7][CH2:8][CH2:9][CH3:10])=[N:4][C:3]=1[CH:11]=[O:12].[C:13](=O)(O)[O-].[K+].BrC[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]=1[C:32]([O:34][CH3:35])=[O:33].O>CN(C)C=O>[Br:1][C:2]1[N:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH3:10])[N:4]([CH2:13][C:29]2[CH:28]=[CH:27][C:26]([C:22]3[C:21]([C:32]([O:34][CH3:35])=[O:33])=[CH:20][CH:25]=[CH:24][CH:23]=3)=[CH:31][CH:30]=2)[C:3]=1[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 100141011H-Imidazole-4-carboxaldehyde, 5-bromo-2-butyl-HCID 19608489Methyl bromomethyl-(1,1'-biphenyl)-2-carboxylate

Product 1

HCID 19370631Methyl 4'-[[4-bromo-2-butyl-5-formyl-1H-imidazol-1-yl]-methyl]-(1,1'-biphenyl)-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.7 g of the product of Step B were introduced into 50 ml of dimethylformamide and 2.46 g of potassium bicarbonate were added with stirring. Then, the mixture stood for about 5 minutes and 5.86 g of methyl bromomethyl-(1,1'-biphenyl)-2-carboxylate (prepared according to EP 0,253,310) in 55 ml of dimethylformamide were added. The mixture stood for 3 days at ambient temperature and the reaction medium was hydrolyzed with 100 ml of water, then extracted with ethyl acetate. The extracts were washed with water saturated with sodium chloride, dried, filtered and evaporated. After chromatography, (eluant: ethyl acetate 5-methylene chloride 95), 6.36 g of the expected product were recovered.

Workup

  1. additionwere added
  2. waitThe mixture stood for 3 days at ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water saturated with sodium chloride
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customAfter chromatography, (eluant: ethyl acetate 5-methylene chloride 95), 6.36 g of the expected product were recovered

Sources & evidence

ORD record
ord-0e2f252bb2d244dd9979c1d794046e07
Source dataset
uspto-grants-1995_02
Patent number
US05389634

Reaction notes

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