1-phenyl-1H-imidazo[4,5-c]pyridine → 1-phenyl-1H,4H,5H,6H,7H-imidazo[4,5-c]pyridine

HRID 2177577Notes

Reaction equation

HRID 2177577 reaction equation
[C:1]1([N:7]2[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)=O.[Rh]>[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 53284731-phenyl-1H-imidazo[4,5-c]pyridine

Product 1

HCID 131502561-phenyl-1H,4H,5H,6H,7H-imidazo[4,5-c]pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of Intermediate 2 (111 mg, 0.569 mmol) in AcOH (15 ml) was passed through a Rh/C catalyst cartridge on an H-Cube hydrogenation apparatus at a pressure of 80 bar and a flow rate of 1 ml/min at 100° C. The reaction was looped through the apparatus for 2 h. The crude reaction mixture was concentrated and purified on 12 g SiO2 column with 0-10% NH3/MeOH CH2Cl2 to give the desired compound (90 mg, 80%). MS (ESI): mass calcd. for C12H13N3, 199.3. m/z found, 200.2 [M+H]+.

Workup

  1. customat 100° C
  2. customThe crude reaction mixture
  3. concentrationwas concentrated
  4. custompurified on 12 g SiO2 column with 0-10% NH3/MeOH CH2Cl2

Sources & evidence

ORD record
ord-d2d5b100715341eaa0d7dc69abb5de35
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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