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

HRID 2177575Notes

Reaction equation

HRID 2177575 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>[C:1]1([N:7]2[C:15]3[CH:14]=[CH: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

3

Reactant 1

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

Product 1

HCID 904084851-phenyl-4,5-dihydro-1H-imidazo[4,5-c]pyridineYield 17.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of Intermediate 2 (196 mg, 1.00 mmol) in AcOH (25 ml) was passed through a Pt2O 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 5 h. The crude reaction mixture was concentrated and purified on 16 g SiO2 column with 0-10% NH3MeOH CH2Cl2 to give the desired compound (35 mg, 17%). MS (ESI): mass calcd. for C12H11N3, 197.1. m/z found, 198.2 [M+H]+.

Workup

  1. customat 100° C
  2. customThe crude reaction mixture
  3. concentrationwas concentrated
  4. custompurified on 16 g SiO2 column with 0-10% NH3MeOH CH2Cl2

Sources & evidence

ORD record
ord-bfe24316273546288ecd96fd7c27f32f
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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