1,1'-Carbonyldiimidazole → 1-Methyl-1h-imidazo[4,5-b]pyridin-2(3h)-one
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]>>[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
4
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
- concentrationThe reaction mixture was concentrated in vacuo
- customThe residue was purified by column chromatography (silica gel, eluted with 0%-100% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-6a9b89f4ab4c4e9ebc10415415934c8f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846713B2
Reaction notes
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