Formic Acid → 2-(3-Hydroxypropyl)-3-methylimidazo[5,4-b]pyridine

HRID 333751Notes

Reaction equation

HRID 333751 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:20]([CH3:21])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=1)C1C=CC=CC=1.C(O)=O>CO.[OH-].[OH-].[Pd+2]>[CH3:21][N:20]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=[C:12]1[CH2:11][CH2:10][CH2:9][OH:8]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 895868242-[3-(benzyloxy)propyl]-3-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 105838782-(3-Hydroxypropyl)-3-methylimidazo[5,4-b]pyridineYield 81.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[3-(benzyloxy)propyl]-3-methyl-3H-imidazo[4,5-b]pyridine (1.8 g), 20% palladium hydroxide on carbon (2.35 g, containing water (50%)), and formic acid (8.45 mL) in methanol (84.5 mL) was refluxed for 6 hr. The mixture was allowed to cool to room temperature, and the catalyst was filtered off. The obtained filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.0 g).

Workup

  1. temperaturewas refluxed for 6 hr
  2. filtrationthe catalyst was filtered off
  3. concentrationThe obtained filtrate was concentrated under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e69391e5075345eab907c8ca47d0f626
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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