p-Fluoronitrobenzene → HCID 23155053, compound

HRID 1912753Notes

Reaction equation

HRID 1912753 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1>CN(C)C=O.O>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([N:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[N:1]=[CH:2]2)=[CH:18][CH:19]=1)([O-:25])=[O:24].[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[N:3]=[CH:2]2)=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

7

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178419860HCID 178419860, compound

Product 2

HCID 23154930HCID 23154930, compoundYield 8%HCID 23155053HCID 23155053, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 3 mL of dimethylformamide, 119 mg (1.00 mmol) of imidazo[4,5-c]pyridine was dissolved, and 138 mg (1.00 mmol) of potassium carbonate and 141 mg (1.00 mmol) of 4-fluoronitrobenzene were added thereto and the mixture solution was stirred at 80° C. for two hours. The solution was diluted with 10 mL of water, and the formed precipitate was collected by filtration, washed with water, and vacuum dried. The obtained crude product was separated by a silica gel column (Si-10, a product of Kusano Co., Ltd., column 30 cm, dichloromethane:methanol=15:1) to obtain 18.9 mg (8%) of 3-(4-nitrophenyl)-3H-imidazo[4,5-c]pyridine and 66.6 mg (28%) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine as yellow solids, respectively.

Workup

  1. filtrationthe formed precipitate was collected by filtration
  2. washwashed with water, and vacuum
  3. customdried
  4. customThe obtained crude product
  5. customwas separated by a silica gel column (Si-10

Sources & evidence

ORD record
ord-63a03177799243a8b0ce357a8ba33a3c
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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