Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2-Bromopyridine | HCID 7973 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 89524833 | HCID 89524833 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 89524760 | HCID 89524760 | 21% |
Reaction Steps
To a solution of 2-bromopyridine (410 mg, 2.6 mmol) in ether (10 mL) was added 2.5M n-BuLi (1.04 mL, 2.6 mmol) dropwise and the solution was stirred at −78° C. for 45 minutes. Then a solution of Example 265C (500 mg, 2.0 mmol) in ether (2 mL) was added to the solution at −78° C. and the mixture was stirred for 2 hours. 1N HCl aqueous solution was added to the mixture till pH<7 and the resulting solution was stirred at room temperature for 1 hour. The reaction mixture was basified with aqueous solution of NaHCO3 and the solution was extracted with EtOAc (20 mL×3). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated to obtain the title compound (140 mg, 21% yield) as a yellow oil. MS: m/z 275 (M−55).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772500B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-a7fabdd10dfc4c708a88fe296b1f672d |
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| Source note | uspto-grants-2014_07 |
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