1,1'-Carbonyldiimidazole → 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

HRID 1044207Notes

Reaction equation

HRID 1044207 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1.C1N=CN([C:15](N2C=NC=C2)=[O:16])C=1>C1COCC1>[CH3:1][N:2]1[C:3]2=[N:4][CH:5]=[CH:6][CH:7]=[C:8]2[NH:9][C:15]1=[O:16]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 123436692-N-methylpyridine-2,3-diamine

Product 1

HCID 9112333-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-oneYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N2-methylpyridine-2,3-diamine (7 g) and CDI (13.82 g) in THF (100 mL) was refluxed for 5 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane) to give 3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (7 g) as a light brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-cd605535aeff4ec3ae25a37157c57401
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

Loading…