[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]benzylamine → 5-Methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-ylamine

HRID 1792266Notes

Reaction equation

HRID 1792266 reaction equation
C[C:2]1[N:3]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11]CC1C=CC=CC=1)[CH:7]=[C:6]([CH3:19])[N:5]=2>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:19][C:6]1[N:5]=[C:4]2[N:3]([C:20]3[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])[CH:2]=[N:10][C:9]2=[C:8]([NH2:11])[CH:7]=1

Participants

4

Reactant 1

HCID 22034103[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]benzylamine

Product 1

HCID 220341085-Methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-ylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

Add palladium hydroxide (0.05 g) to a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]benzylamine (0.15 g, 0.42 mmol) in acetic acid (10 mL). Hydrogenate the mixture at a pressure of 50 psi for 20 hr. Filter the reaction mixture through celite, evaporate to dryness under reduced pressure, dilute with EtOAc and successively wash with aq NaHCO3 and aq NaCl. Dry the organic layer over Na2SO4, filter, and concentrate. Purify by flash column chromatography (3% MeOH in CH2Cl2) to obtain the title compound as a brown solid.

Workup

  1. filtrationFilter the reaction mixture through celite
  2. customevaporate to dryness under reduced pressure
  3. additiondilute with EtOAc
  4. washsuccessively wash with aq NaHCO3 and aq NaCl
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by flash column chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ed258c7e10b54f8bb28c48f09d702f3d
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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