HCID 23154955, compound → HCID 23155133, compound

HRID 1912861Notes

Reaction equation

HRID 1912861 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([C:19]#[N:20])[C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([C:19]#[N:20])[C:13]=3[N:12]=[CH:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 23154955HCID 23154955, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23155133HCID 23155133, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 100 mL of methanol, 240 mg (0.9 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile was dissolved, and 170 mg of 10% palladium carbon was added thereto and the mixture solution was refluxed with stirring in a hydrogen atmosphere for one hour. The palladium carbon was removed by Celite filtration and the reaction solution was concentrated under reduced pressure, and the obtained crude product was purified by a silica gel column (dichloromethane:methanol=40:1) to obtain 65 mg (30%) of a target product as a pale yellow solid.

Workup

  1. temperaturethe mixture solution was refluxed
  2. customThe palladium carbon was removed by Celite filtration
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe obtained crude product
  5. customwas purified by a silica gel column (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-467a6b585a6f4afa9c2e75cbf4641ffe
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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