Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,4-Dichloropyridine | HCID 33515 | — |
| Reactant | Isopropyl 4-Hydroxypiperidine-1-carboxylate | HCID 16745126 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66893855 | HCID 66893855 | — |
| Product | HCID 86626960 | HCID 86626960 | — |
Reaction Steps
2,4-Dichloropyridine (0.52 g, 3.5 mmol) in 2 mL of DMF was added to a suspension of sodium hydride (60% in oil, 0.16 g, 3 eq) and 2a (0.55 g, 3 mmol) in 8 mL of DMF. The mixture was heated at 90° C. The mixture was allowed to cool to room temperature, water was added to quench the excess sodium hydride and the solution was extracted with ethyl acetate twice, washed with a saturated solution of sodium bicarbonate, dried and evaporated. The crude material was purified on silica gel (eluent: 20% then 50% of ethyl acetate in hexane) to give 10a and 10b (0.55 g of the more polar product and 84 mg of the less polar product).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08481731B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-5b1821d060924fab9159672b1d09f748 |
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| Source note | uspto-grants-2013_07 |
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