Potassium Carbonate → HCID 19373082, compound

HRID 1748495Notes

Reaction equation

HRID 1748495 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[CH3:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.CNC1CCCCC1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([C:3]([OH:2])=[O:4])=[CH:6]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 19373082HCID 19373082, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

Indole-3-carboxylic acid methyl ester (2.50 g), 4-methyl-iodobenzene (3.72 g), copper (I) iodide (136 mg), N,N′-dimethyl-1,2-cyclohexanediamine (0.5 ml) and potassium carbonate (4.06 g) were stirred at 120° C. for 48 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was dissolved in ethanol (10 ml), sodium hydroxide (1.17 g) was added and stirred at room temperature overnight. The reaction solution was concentrated with an evaporator, the aqueous layer was acidified by the addition of 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the titled compound (184 mg) as a dark brown solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethanol (10 ml)
  6. additionsodium hydroxide (1.17 g) was added
  7. concentrationThe reaction solution was concentrated with an evaporator
  8. additionthe aqueous layer was acidified by the addition of 1N hydrochloric acid aqueous solution
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-66a45327182d449a9c083f8d88854531
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…