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

HRID 1044202Notes

Reaction equation

HRID 1044202 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[CH3:13][NH:14][C:15]1[C:16]([NH2:21])=[N:17][CH:18]=[CH:19][CH:20]=1.[Cl-].[Cl-].[Ca+2]>C1COCC1>[CH3:13][N:14]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:21][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5284359Calcium ChlorideHCID 122384043-N-methylpyridine-2,3-diamine

Product 1

HCID 8542361-Methyl-1h-imidazo[4,5-b]pyridin-2(3h)-oneYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

CDI (2.251 g) was added to a solution of N3-methylpyridine-2,3-diamine (1.14 g) in THF (dry) (50 ml) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) over weekend. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane) to give 1-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1.1 g) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6179fd5192f049e1bf6dde27488aea31
Source dataset
uspto-grants-2013_10
Patent number
US08563575B2

Reaction notes

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