1-Bromo-2-iodobenzene → HCID 67203694, compound

HRID 1472508Notes

Reaction equation

HRID 1472508 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.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:1]=[N:2][CH:3]=[CH:4][C:5]1=2

Participants

6

Reactant 3

HCID 114151-Bromo-2-iodobenzeneHCID 11430Potassium CarbonateHCID 130802gamma-Carboline

Product 1

HCID 67203694HCID 67203694, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 84.1 g (500 mmol) of 5H-pyrido[4,3-b]indole [244-69-9], 147.1 g (520 mmol) of 2-bromoiodobenzene [583-55-1], 103.7 g (750 mmol) of potassium carbonate, 31.8 g (500 mmol) of copper powder and 300 g of glass beads (diameter 3 mm) in 800 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 1500 ml of dichloromethane, and the solution is washed three times with 500 ml of concentrated ammonia solution each time and dried over magnesium sulfate. After removal of the dichloromethane in vacuo, the oily residue is distilled in a short-path evaporator (p=5×10−3 mbar, T=120° C.). Yield: 56.1 g (173 mmol), 35%; purity: 98% (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 1500 ml of dichloromethane
  6. washthe solution is washed three times with 500 ml of concentrated ammonia solution each time
  7. dry with materialdried over magnesium sulfate
  8. customAfter removal of the dichloromethane in vacuo
  9. distillationthe oily residue is distilled in a short-path evaporator (p=5×10−3 mbar, T=120° C.)

Sources & evidence

ORD record
ord-f9f31eb5716043ce92564024979ab72d
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

Loading…