Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-butyl N-(pyrrolidin-3-yl)carbamate | HCID 2757234 | — |
| Reactant | 5-Bromo-2-fluoropyridine | HCID 2783168 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66673555 | HCID 66673555 | 36% |
Reaction Steps
5-Bromo-2-fluoropyridine (1.76 mg, 10 mmol) and 3.62 g (10 mmol) of tert-butyl pyrrolidin-3-ylcarbamate were dissolved in 20 ml of N,N-dimethylformamide. Potassium carbonate (1.38 g, 10 mmol) was added to the solution, and the mixture was stirred at 100° C. for 6 hr. Ethyl acetate (60 ml) and 8.5 ml of water were added to the reaction solution, and the organic layer was washed five times with 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and was filtered. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give 1.23 g (yield 36%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07867980B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-d2fca95e96044d369ede5be188ff12be |
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| Source note | uspto-grants-2011_01 |
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