4-Fluoroiodobenzene → HCID 9796673, compound

HRID 2084064Notes

Reaction equation

HRID 2084064 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1>CN1C(=O)CCC1.ClCCl.[Cu]>[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:14]2[C:15]3[C:11](=[CH:10][CH:9]=[C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH:16]=3)[CH:12]=[CH:13]2)=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 98157856-(4-methylpiperazin-1-yl)-1H-indole

Product 1

HCID 9796673HCID 9796673, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 6-(4-Methylpiperazinyl)-indole (14.8 mg, 0.0687 mmol), K2CO3 (37.9 mg, 0.275 mmol), CuBr (4.9 mg, 0.0353 mmol), a little copper powder and 1-Fluoro-4-iodobenzene (30.5 mg, 0.37 mmol) in 1 ml of NMP was heated at 170° C., under argon, overnight. After cooling, the mixture was diluted with dichloromethane and the organic layer washed with water 10 times before being passed through a silica gel column (eluting with 1% 2M ammonia/methanol in dichloromethane) to give the title product (7.8 mg, 37%).

Workup

  1. temperatureAfter cooling
  2. washthe organic layer washed with water 10 times
  3. washbefore being passed through a silica gel column (eluting with 1% 2M ammonia/methanol in dichloromethane)

Sources & evidence

ORD record
ord-92e8faec6a31461f9ed950b0d7f6a550
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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