Water → 1-Benzyl-6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester

HRID 1583369Notes

Reaction equation

HRID 1583369 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([CH2:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1)[CH:10]=2)=[O:6].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([CH2:16][C:17]1[NH:21][CH:20]=[CH:19][N:18]=1)[CH:10]=2)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 70479574HCID 70479574, compound

Product 1

HCID 704795811-Benzyl-6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.17 g. of 50% dispersion in mineral oil) was added portionwise to a stirred solution of 6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester (0.90 g.) in dry N,N-dimethylformamide (50 ml.) and the mixture was stirred at room temperature for 1 hour. Benzyl bromide (0.61 g.) was added and the resulting mixture was stirred for 2 hours and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed well with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform first gave mineral oil followed by pure product. Evaporation of the product-containing fractions gave a solid which was crystallized from ethyl acetate/petrol (b.p. 60°-80°) to give 1-benzyl-6-(1-imidazolylmethyl)indole-2-carboxylic acid methyl ester, m.p. 120°-122° C.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. washthe combined extracts were washed well with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customwas chromatographed on silica gel
  8. washElution with chloroform first gave mineral oil
  9. customEvaporation of the product-containing fractions
  10. customgave a solid which
  11. customwas crystallized from ethyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-6db14b19df7a403bbc5b73de402adb6c
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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