Potassium Carbonate → HCID 70665120, compound

HRID 1472506Notes

Reaction equation

HRID 1472506 reaction equation
[CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][N:2]=1.I[C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]>[CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]([C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([O:19][CH3:20])=[O:18])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 130802gamma-Carboline

Product 1

HCID 70665120HCID 70665120, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 16.8 g (100 mmol) of 5H-pyrido[4,3-b]indole [244-69-9], 28.8 g (110 mmol) of methyl 2-iodobenzoate [610-97-9], 34.6 g (250 mmol) of potassium carbonate, 6.4 g (100 mmol) of copper powder and 100 g of glass beads (diameter 3 mm) in 300 ml of DMF is stirred at 130° C. for 24 h. After cooling, the mixture is filtered through a short Celite bed, the bed is rinsed with DMF, and the latter is removed in vacuo. The residue is dissolved in 500 ml of dichloromethane, and the solution is washed three times with 200 ml of 0.5 N sodium hydroxide solution each time and dried over magnesium sulfate. After removal of the dichloromethane in vacuo, the residue is recrystallised once from ethyl acetate and dried in vacuo (p=0.1 mbar, T=60° C.). Yield: 19.3 g (64 mmol), 64%; purity: 97% (1H-NMR).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered through a short Celite bed
  3. washthe bed is rinsed with DMF
  4. customthe latter is removed in vacuo
  5. dissolutionThe residue is dissolved in 500 ml of dichloromethane
  6. washthe solution is washed three times with 200 ml of 0.5 N sodium hydroxide solution each time
  7. dry with materialdried over magnesium sulfate
  8. customAfter removal of the dichloromethane in vacuo
  9. customthe residue is recrystallised once from ethyl acetate
  10. customdried in vacuo (p=0.1 mbar, T=60° C.)

Sources & evidence

ORD record
ord-85858f38943c4aab8a088abc9ab8eade
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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