Imidazole → 1-Acetyl-2-[1-imidazolylmethyl]-3-methylindole-5-carboxylic acid ethyl ester

HRID 280618Notes

Reaction equation

HRID 280618 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15](=[O:17])[CH3:16])[C:10]([CH2:18]Br)=[C:9]2[CH3:20])=[O:5])[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15](=[O:17])[CH3:16])[C:10]([CH2:18][C:22]1[NH:21][CH:25]=[CH:24][N:23]=1)=[C:9]2[CH3:20])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 516892Sodium BicarbonateHCID 136630561-Acetyl-2-bromomethyl-3-methylindole-5-carboxylic acid ethyl ester

Product 1

HCID 704571821-Acetyl-2-[1-imidazolylmethyl]-3-methylindole-5-carboxylic acid ethyl esterYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-acetyl-2-bromomethyl-3-methylindole-5-carboxylic acid ethyl ester (5.74 g), imidazole (11.56 g), sodium bicarbonate (2.9 g) and acetone was stirred for 18 hours and then evaporated. The residue was partitioned between water and ethyl acetate. The ethyl acetate layer was separated, washed with water and dried (Na2SO4). The solvent was evaporated and the residue was chromatograhed on silica gel. Elution with chloroform first gave some impurity followed by pure product. Evaporation of the product-containing fractions gave 1-acetyl-2-[1-imidazolylmethyl]-3-methylindole-5-carboxylic acid ethyl ester (4.80 g) which was used without further characterisation.

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. washElution with chloroform
  8. customfirst gave some impurity
  9. customEvaporation of the product-containing fractions

Sources & evidence

ORD record
ord-c962ad83fb5d49bea502525e8232e6f9
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…