Triethylamine → HCID 54355981, compound

HRID 1731752Notes

Reaction equation

HRID 1731752 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14](I)=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(N(CC)CC)C.[C:28]1(=[O:34])[CH2:33][CH2:32][CH2:31][CH:30]=[CH:29]1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([C:30]1[CH2:31][CH2:32][CH2:33][C:28](=[O:34])[CH:29]=1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135942-Cyclohexen-1-oneHCID 13371549HCID 13371549, compound

Product 1

HCID 54355981HCID 54355981, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

In a pressure vessel, 1.08 g (3 mmol) of 6-iodo-4-methyl-β-carboline-3-carboxylic acid ethyl ester is heated to 140° C. for 3 hours with 72 mg (0.06 mmol) of palladium(II) acetate, 0.48 ml (3.6 mmol) of triethylamine, and 432 mg (4.5 mmol) of 2-cyclohexen-1-one in 10 ml of absolute dimethylformamide. After concentration, the mixture is chromatographed over silica gel with methylene chloride:ethanol=10:2. After recrystallization of the combined polar fractions from methylene chloride/cyclohexane, 75 mg (6.7% of theory) of 6-(1-oxo-2-cyclohexen-3-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester is obtained, mp 245°-248° C. After recrystallization from ethyl acetate, the combined nonpolar fractions, which are chromatographed twice over silica gel with toluene:glacial acetic acid:water=10:10:1, yield 60 mg (5.8% of theory) of 6-(1-oxocyclohex-3-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 182°-189° C.

Workup

  1. concentrationAfter concentration
  2. customthe mixture is chromatographed over silica gel with methylene chloride
  3. customAfter recrystallization of the combined polar fractions from methylene chloride/cyclohexane

Sources & evidence

ORD record
ord-ac83de4e30bb498cac44615c2e0b9235
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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