Potassium Carbonate → Methyl 1-(7-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

HRID 1869173Notes

Reaction equation

HRID 1869173 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:23]>CC(N(C)C)=O.C(OCC)(=O)C.O>[CH3:20][O:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)[CH:25]=1)=[O:23]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 589098Methyl indole-3-carboxylateHCID 106078294-Chloro-7-methoxyquinoline

Product 1

HCID 68971128Methyl 1-(7-methoxyquinolin-4-yl)-1H-indole-3-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

3.46 g (25 mmol) of potassium carbonate and 1.94 g (10 mmol) of 4-chloro-7-methoxyquinoline are added to 1.75 g (10 mmol) of 3-methoxycarbonyl-1H-indole in 50 cm3 of dimethylacetamide under an argon atmosphere. After stirring at a temperature in the region of 140° C. for 20 hours, the reaction mixture is cooled and diluted with 300 cm3 of ethyl acetate and 300 cm3 of water. The organic phase is separated off by settling and washed with three times 300 cm3 of water and 300 cm3 of saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (8/2 and then 7/3 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), 1.7 g of 3-methoxycarbonyl-1-(7-methoxyquinol-4-yl)-1H-indole are obtained in the form of a yellow foam. Mass spectrum (EI): m/e 332 (M+•), m/e 301.

Workup

  1. temperaturethe reaction mixture is cooled
  2. customThe organic phase is separated off by settling
  3. washwashed with three times 300 cm3 of water and 300 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialit is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is purified by flash chromatography [eluent
  8. concentrationAfter concentrating the fractions to dryness under reduced pressure (2.7 kPa), 1.7 g of 3-methoxycarbonyl-1-(7-methoxyquinol-4-yl)-1H-indole
  9. customare obtained in the form of a yellow foam

Sources & evidence

ORD record
ord-98630008919a493cbc2699f7630d6616
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

Loading…