[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 2121596Notes

Reaction equation

HRID 2121596 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-15dd7ac7738542fb968e38f6aa9bc7db
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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