(Trimethylsilyl)imidazole → HCID 70479574, compound

HRID 648047Notes

Reaction equation

HRID 648047 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6](C(=O)C)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH2:14]Br)[CH:8]=2)=[O:4].C[Si](C)(C)[N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>C1(C)C=CC=CC=1.N.C(O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH2:14][C:22]1[NH:21][CH:25]=[CH:24][N:23]=1)[CH:8]=2)=[O:4]

Participants

6

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 13662988HCID 13662988, compound

Product 1

HCID 70479574HCID 70479574, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 1-acetyl-6-bromomethylindole-2-carboxylic acid methyl ester (3.1 g.) in toluene (25 ml.) was added dropwise with stirring to a solution of 1-trimethylsilylimidazole (5.60 g.) in toluene (25 ml.) at 80° C. The mixture was stirred at 80° for 2 hours and then evaporated. Water was added and the mixture was extracted several times with ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated to give an oil which was dissolved in a concentrated solution of ammonia in ethanol (40 ml.). The solution was allowed to stand at room temperature for 2.5 hours and then evaporated and the residue was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallized from ethyl acetate to give 6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester (1.49 g.), m.p. 204°-205° C.

Workup

  1. customevaporated
  2. additionWater was added
  3. extractionthe mixture was extracted several times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil which
  8. waitto stand at room temperature for 2.5 hours
  9. customevaporated
  10. customthe residue was chromatographed on silica gel
  11. washElution with chloroform
  12. customgave a solid which
  13. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-380144a5273041eabf72607cc2af6a13
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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