2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine → 4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamine

HRID 1492610Notes

Reaction equation

HRID 1492610 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:23])[CH:3]=1>CO.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:23])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 104031282-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 100165294-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamineYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6.81 g (21.0 mmol) of the product of Step A dissolved in 75 mL methanol in a high pressure reaction vessel was added 0.3 g 5% palladium on carbon. The resulting suspension was pressurized to 40 psi with H2 and shaken for 2 hours. The solution was filtered through a pad of celite and the filtrate concentrated to a gray-green oil which crystallized on standing. The crude material was flash chromatographed with 50% ethyl acetate/hexane and 3% methanol/ethyl acetate to yield 5.0 g (85%) of the title compound.

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. concentrationthe filtrate concentrated to a gray-green oil which
  3. customcrystallized
  4. customchromatographed with 50% ethyl acetate/hexane and 3% methanol/ethyl acetate

Sources & evidence

ORD record
ord-20da09ea741e45bc94fe03af818748a1
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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