Sodium Chloride → Ethyl 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate
Reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CN(C=O)C>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21][O:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
20.00 g (85.38 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 17A were initially charged with 19.44 g (93.91 mmol) of 2,6-difluorobenzyl bromide and 61.20 g (187.83 mmol) of caesium carbonate in 1.18 l of DMF and stirred at 60° C. for 5 h. The flask content was poured 6.4 l of 10% strength aqueous sodium chloride solution and extracted twice with ethyl acetate. The combined organic phases were washed once with 854 ml of 10% strength aqueous sodium chloride solution, dried, evaporated and dried under high vacuum at RT overnight. This gave 28.2 g (92% of theory; purity about 90%) of the title compound.
Workup
- extractionextracted twice with ethyl acetate
- washThe combined organic phases were washed once with 854 ml of 10% strength aqueous sodium chloride solution
- customdried
- customevaporated
- customdried under high vacuum at RT overnight
Sources & evidence
- ORD record
- ord-9b758bf9e944438eb0bf4c80fd531faf
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796305B2
Reaction notes
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