Potassium Carbonate → Methyl 5-methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylate

HRID 492189Notes

Reaction equation

HRID 492189 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1>CS(C)=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:20])[CH:18]=2)[N:13]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 691404-ChloroquinolineHCID 2759866Methyl 5-methyl-1H-indole-3-carboxylate

Product 1

HCID 68968705Methyl 5-methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

1.65 g (11.9 mmol) of potassium carbonate are added at 25° C. under an argon atmosphere to 0.9 g (4.75 mmol) of 3-methoxycarbonyl-5-methyl-1H-indole in 10 cm3 of dimethyl sulphoxide. After stirring at 25° C. for 0.5 hour, 0.623 cm3 (4.75 mmol) of 4-chloroquinoline is added. After stirring at 100° C. for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 of ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.4 g of a residue which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (7/3 by volume)]. After concentrating the fractions under reduced pressure, 1.2 g of 3-methoxycarbonyl-5-methyl-1-(quinol-4-yl)-1H-indole are obtained in the form of a white solid melting at 168° C.

Workup

  1. stirringAfter stirring at 100° C. for 48 hours
  2. temperaturethe reaction mixture is cooled
  3. washwashed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution
  4. customAfter separating the phases
  5. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-c6cb50011c7d426288f78be0f814ded1
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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