Sodium hydride → 1-ethyl-3-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587464Notes

Reaction equation

HRID 587464 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1C(OCC)=O.[H-].[Na+].[CH2:18]([N:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)[C:21]1=[O:36])[CH3:19].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH2:18]([N:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22]([C:29]2[CH:30]=[CH:31][C:32]([O:35][C:2]3[N:3]=[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][N:5]4[CH:10]=3)=[CH:33][CH:34]=2)[C:21]1=[O:36])[CH3:19]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 21643308Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylateHCID 585777461-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 585773621-ethyl-3-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 11%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (220 mg), NaH (70 mg) and 1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (255 mg) in DMF (2 mL) was stirred at 100° C. under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was diluted with MeOH and concentrated under reduced pressure. The residue was purified by column chromatography (NH silica gel, eluted with 0%-30% EtOAc in hexane) to give 1-ethyl-3-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (40 mg) as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-e501fdcb1ea44b23ae5b7550d4374984
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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