Dimethyl Sulfoxide → ethyl 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C(N([CH2:17][CH3:18])CC)C.[C]=O.[CH3:21][OH:22].CS(C)=[O:25]>C(O)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)([O:25][CH2:17][CH3:18])=[O:22]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 95 °C
Procedure
To a mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) in dimethylsulfoxide (1 ml) and ethanol (5 ml) in Parr bomb were added triethylamine (0.31 ml, 2.25 mmol), palladium acetate (33.7 mg, 0.15 mmol), and 1,3-(bisdiphenylphosphino)propane (61.9 mg, 0.15 mmol). Carbon monoxide gas (40 atm) was applied and the reaction mixture was heated at 95° C. for 18 hours with vigorously stirring. The reaction mixture was diluted with diethyl ether (50 ml) and washed with water (10 ml). The aqueous layer was thoroughly extracted with diethyl ether. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with methanol yielded 5-(carboethoxy)-7-azaoxindole as a tan solid (53 mg, 25.7%).
Workup
- washwashed with water (10 ml)
- extractionThe aqueous layer was thoroughly extracted with diethyl ether
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- filtrationfiltered
- customevaporated under vacuum
- customto give crude product
Sources & evidence
- ORD record
- ord-3300dd98ecf848edbea8e3ea5c312ce3
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350747B1
Reaction notes
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