Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Methyl 2-oxocycloheptane-1-carboxylate | HCID 288225 | — |
| Reactant | 2-Amino-4-bromopyridine | HCID 693282 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 58574318 | HCID 58574318 | 69.4% |
Reaction Steps
A mixture of methyl 2-oxocycloheptanecarboxylate (2 g, 11.8 mmol) and 4-bromopyridin-2-amine (2.04 g, 11.8 mmol), and PPA (5 mL) in 1,2-dichloroethane (10 mL) was stirred at 85° C. for 5 h. The reaction mixture was cooled to ambient temperature. A chilled saturated sodium carbonate solution was added to adjust pH to 8. The resulting mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel chromatography to produce 2.4 g of the desired product. MS (ESI): 293 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772301B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-7821c82344c340d1882bdbd44321c820 |
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| Source note | uspto-grants-2014_07 |
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