Sodium Carbonate → 3-Bromo-2-butylimidazo[1,2-a]pyridine
Reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]2[CH:13]=1)[CH2:2][CH2:3][CH3:4].[Br:14]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:14][C:13]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A mixture of 3.5 g of the product of Stage C and 50 ml of chloroform was cooled to 10° C. and 4.55 g of N-bromo succinimide were added. The mixture was stirred at this temperature for 30 minutes and was then poured into a saturated solution of sodium carbonate and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried, filtered and evaporated to dryness to obtain after chromatography on silica (methylene chloride: 95/methanol: 5), 3.8 g of the expected product in the form of a black oil.
Workup
- extractionextracted with ethyl acetate
- washThe extracts were washed with a saturated aqueous solution of sodium chloride
- customdried
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-1ea163b323a740aaab63a2aa7ac99d06
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420138
Reaction notes
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