Ethyl 2-chloroacetoacetate → 3-Carboethoxy-2,6-dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyridine
Reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])=[CH:6][C:5]([CH3:18])=[CH:4][N:3]=1.Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[C:21]([C:20]1[N:3]2[CH:4]=[C:5]([CH3:18])[CH:6]=[C:7]([O:8][CH2:9][C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=3[CH3:17])[C:2]2=[N:1][C:26]=1[CH3:28])([O:23][CH2:24][CH3:25])=[O:22]Participants
4
Procedure
A mixture of 2-amino-3-(2,6-dimethylbenzyloxy)-5-methylpyridine (1.0 g, 4.13 mmol) and ethyl 2-chloroacetoacetate (0.79 g, 4.55 mmol) in 20 ml abs. ethanol was refluxed for 19 h. More ethyl 2-chloroacetoacetate (0.25 g) was added. The reaction mixture was refluxed for additional 23 h. The solvent was evaporated in vacuo and the residue was dissolved in methylene chloride and washed with aqueous NaHCO3. The organic layer was dried and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using methylene chloride:ethyl acetate (100:10) as eluent to give 0.68 g (47%) of the title compound.
Workup
- temperatureThe reaction mixture was refluxed for additional 23 h
- customThe solvent was evaporated in vacuo
- dissolutionthe residue was dissolved in methylene chloride
- washwashed with aqueous NaHCO3
- customThe organic layer was dried
- customevaporated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-14b989392aea4a51b7a3bbb852c47bbf
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265415B1
Reaction notes
Loading…