Water → HCID 117700521, compound

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%).

1. customThe mixture thus obtained
2. waitat 80° C. for 3 hours
3. customthe mixture thus obtained
4. stirringwas then stirred at 80° C. for 2 hours
5. extractionthe mixed solution was then extracted with ethyl acetate three times
6. customThe organic layer thus obtained
7. dry with materialwas dried over anhydrous magnesium sulfate
8. distillationthe solvent was then distilled away under reduced pressure
9. customThe residue thus obtained
10. customwas purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1, v/v)

ORD record

ord-ff160800a11d468fb878e7ccf77cc7a6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975263B2