Potassium Carbonate → HCID 54369859, compound

HRID 1608930Notes

Reaction equation

HRID 1608930 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[NH:19]2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[Cu]Br>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[N:19]2[C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 47169039HCID 47169039, compound

Product 1

HCID 54369859HCID 54369859, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 1049PyridineSolventHCID 7416NitrobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

4-Bromoveratrole (5.7 g, 26 mmol), 6-chloroindole-2-carboxylic acid morpholide (1.7 g, 6.5 mmol), potassium carbonate (1.7 g), copper(I) bromide (0.2 g) in a mixture of pyridine (2 ml) and nitrobenzene was stirred at 140° C. for 14 hours. After cooling to room temperature, the reaction mixture was applied onto a flash chromatography column (silica gel, 140 g), Elution with toluene, toluene/acetone [9:1] and toluene/acetone [8:2] (500 ml each) gave 6-chloro-1-(3,4-dimethoxyphenyl)indole-2-carboxylic acid morpholide as brown oil. Yield: 2.1 g (81% of theoretical) Rf : 0.54 (toluene/acetone, 7:3). The H-NMR spectra was consistent with the assigned structure.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe reaction mixture was applied onto a flash chromatography column (silica gel, 140 g), Elution with toluene, toluene/acetone [9:1] and toluene/acetone [8:2] (500 ml each)

Sources & evidence

ORD record
ord-a33721e21b704016928abe57b8007dfb
Source dataset
uspto-grants-1995_03
Patent number
US05399559

Reaction notes

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