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

HRID 492183
Notes
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Reaction equation

HRID 492183 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)[CH:25]=[CH:24][N: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)[CH:25]=[CH:24][N:23]=2)[CH:12]=1)=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 140539Isoquinoline, 1-chloro-HCID 2759866Methyl 5-methyl-1H-indole-3-carboxylate

Product 1

HCID 68968694Methyl 1-(isoquinolin-1-yl)-5-methyl-1H-indole-3-carboxylateYield 99.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
25 °C

Procedure

1.65 g (11.9 mmol) of potassium carbonate are added at 25° C. under an argon atmosphere to 0.900 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, 0.677 cm3 (4.75 mmol) of 1-chloroisoquinoline 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. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.50 g of a residue which is purified by flash chromatography [eluent: cyclohexane/ethyl acetate (8/2 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), 1.4 g of 3-methoxycarbonyl-1-(isoquinol-1-yl)-5-methyl-1H-indole are obtained in the form of a white solid melting at 142° 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. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6a6015b4e15047c79a56a9aff56e62b4
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531663B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes