Ethyl Acetate → HCID 58577251, compound

HRID 1430055Notes

Reaction equation

HRID 1430055 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]([CH3:25])[C:16]2=[O:26])=[CH:11][CH:10]=1)C1C=CC=CC=1.CCOC(C)=O>CN(C=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]([CH3:25])[C:16]2=[O:26])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 585774663-[4-(benzyloxy)phenyl]-1,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577251HCID 58577251, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[4-(benzyloxy)phenyl]-1,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2.0 g) and 10% Pd—C (0.308 g) in DMF (10 mL)-EtOAc (100 mL) was hydrogenated under balloon pressure at 20° C. for 1 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 50%-100% EtOAc in hexane) to give 3-(4-hydroxyphenyl)-1,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1.30 g) as a light brown solid. This product was subjected to the next reaction without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (NH silica gel, eluted with 50%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-580adf4827e44ae0a7dd6e42705ccc93
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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