4-Fluoroiodobenzene → HCID 9861355, compound

HRID 2084054Notes

Reaction equation

HRID 2084054 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)=[CH: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>CN1CCC(=O)CC1.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]([C:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH:4]=4)[CH:16]=3)[CH:12]=[CH:13]2)=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 101305596-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 9861355HCID 9861355, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 740491-Methyl-4-piperidoneSolvent

Procedure

A mixture of 6-(1-Methyl-1,2,5,6-tetrahydropyridin-4-yl)-indole (20.1 mg, 0.0945 mmol), potassium carbonate (K2CO3; 52.3 mg, 0.3787 mmol), cuprous bromide (CuBr; 6.7 mg, 0.0473 mmol), a little copper powder and 1-fluoro4-iodobenzene (42.04 mg, 0.189 mmol) in 1 ml of N-methyl-4-piperidone (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 (15 mg, 55%).

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-50c43d5d8b8646a98334a5a3a3bf233e
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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