Ethyl Acetate → HCID 67834674, compound

HRID 330167Notes

Reaction equation

HRID 330167 reaction equation
[CH3:1]/[C:2](=[CH:9]\[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)/[C:3]([NH:5][CH2:6][CH2:7][CH3:8])=[O:4].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH3:32][O:31][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][C:21]=1[CH2:20][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10](/[CH:9]=[C:2](/[C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH3:8])\[CH3:1])[CH:11]=2)[NH:15][CH:14]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 14882682HCID 14882682, compound

Product 1

HCID 67834674HCID 67834674, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of E-α-methyl-N-propylindol-5-acrylamide (1.75 g) and silver carbonate (1.99 g) in dry toluene (30 ml) was stirred and heated under reflux for 18 hr, under an atmosphere of nitrogen. The mixture was cooled to 80°, methyl 4-bromomethyl-3-methoxybenzoate (2.06 g) added, and the mixture stirred at 85° for 15 hours. The mixture was cooled, ethyl acetate (50 ml) added, the salts were removed by filtration through diatomaceous earth, the filter pad was washed with ethyl acetate, and the filtrate evaporated. The product was purified by flash chromatography, eluting with 5:2:3 hexane:methylene chloride:ethyl acetate, to give methyl E-3-methoxy-4-[5-[2-(propylcarbamoyl)-1-propenyl]indol-3-ylmethyl]benzoate (1.62 g, 53%) as a solid foam; mp 55°-60°; partial NMR (250 MHz, DMSO-d6): 0.87(t, 3H, CH2CH2CH3), 1.47(m, 2H, CH2CH2CH3), 1.99 (d, J=0.98 Hz, 3H, CCH3), 3.10(m, 2H, CH2CH2CH3), 3.82(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.05(s, 2H, ArCH2Ar'), 7.93(br t, NHCO), 11.0(br s, 1H, H1 -indole).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hr, under an atmosphere of nitrogen
  3. temperatureThe mixture was cooled to 80°
  4. stirringthe mixture stirred at 85° for 15 hours
  5. temperatureThe mixture was cooled
  6. customthe salts were removed by filtration through diatomaceous earth
  7. washthe filter pad was washed with ethyl acetate
  8. customthe filtrate evaporated
  9. customThe product was purified by flash chromatography
  10. washeluting with 5:2:3 hexane

Sources & evidence

ORD record
ord-30b0e677027c462ba15dc3d70b3481b0
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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