Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-6-fluoropyridine | HCID 639438 | — |
| Reactant | D-proline methyl hydrochloride | HCID 117700842 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 117700521 | HCID 117700521 | 16.4% |
Reaction Steps
Triethylamine (1.91 mL, 13.7 mmol) and D-proline methyl hydrochloride (1.13 g, 6.84 mmol) were added to a solution of 2-bromo-6-fluoropyridine (802 mg, 4.55 mmol) in 1,4-dioxane (9 mL) at room temperature. The mixture thus obtained was stirred at the same temperature as above for 30 minutes, and then at 80° C. for 3 hours. Thereafter, triethylamine (951 uL, 6.84 mmol) was further added to the resulting solution at room temperature, and the mixture thus obtained was then stirred at 80° C. for 2 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate three times. The organic layer thus obtained was dried over anhydrous magnesium sulfate, and the solvent was then distilled away under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1, v/v) to obtain the title compound (213 mg, yield: 16%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08975263B2 |
|---|
| Source dataset | uspto-grants-2015_03 |
|---|
| ORD ID | ord-ff160800a11d468fb878e7ccf77cc7a6 |
|---|
| Source note | uspto-grants-2015_03 |
|---|