Triethylamine → (4S,5R)-3-{[3-bromo-6-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]methyl}-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

(4S,5R)-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (1.0721 g, 2.293 mmol), 3,3-difluoroazetidine hydrochloride (1.336 g, 10.32 mmol), triethylamine (3.20 ml, 22.93 mmol) and THF (10 ml) were sealed in a microwave vessel and subject to microwave irradiation at 150° C. for 8 hrs. Volatiles were removed under reduced pressure. The resulting pot residue was worked up with brine/ethyl acetate. The combined extracts were dried over Na2SO4, filtered and evaporated to afford a dark mixture. This dark mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge). The column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate). Related fractions were pooled and evaporated under reduced pressure to afford a light amber glass of 530.8 mg as the titled compound. LCMS calc.=523.03. found=525.99.

1. customsubject to microwave irradiation at 150° C. for 8 hrs
2. customVolatiles were removed under reduced pressure
3. dry with materialThe combined extracts were dried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. customto afford a dark mixture
7. customThis dark mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge)
8. washThe column was eluted by an ethyl acetate/hexanes mixture (0% to 40% ethyl acetate)
9. customevaporated under reduced pressure

ORDレコード

ord-0f3bf028526340709b385917049e6aa0

出典データセット

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09221834B2