Ethyl bromoacetate → 8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester
Reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[C:10]([N:16]=[C:17](SC)[S:18][CH3:19])=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=1.C(N(CC)CC)C>O>[CH2:6]([O:5][C:3]([C:2]1[N:11]2[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([Br:8])[C:10]2=[N:16][C:17]=1[S:18][CH3:19])=[O:4])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Ethyl bromoacetate (5.4 g) was added to methyl N-(3-bromo-5-methyl-2-pyridyl)-(methylsulfanyl)methaneimidothioate, and the mixture was stirred at 60° C. for 4 hours. After cooled to room temperature, triethylamine was added to treat the material, and water was further added thereto. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:9) to give 8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester (2.4 g) as a white powder.
Workup
- temperatureAfter cooled to room temperature
- additionwas further added
- extractionThe reaction mixture was extracted with ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customThe resulting residue was purified by column chromatography (ethyl acetate:n-hexane=1:9)
Sources & evidence
- ORD record
- ord-31144bd7a59048e2bf80aaa8e7f65a5f
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772249B2
Reaction notes
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