4-Acetylpyridine → HCID 71544237, compound

To a stirred solution of 2-(4-fluorophenyl)-1,3,4-oxadiazole (0.8 g, 2.4 mmol) in THF (10 mL) was added LDA (2.9 mmol) at −78° C. (0.308 g, 2.9 mmol) and mixture was stirred for 20 min. A solution of 4-acetyl pyridine (0.377 g, 3.1 mmol) in THF (10 mL) was added at −78° C. and stirred for 2 h. The reaction mixture was quenched with saturated NH4Cl solution (50 mL), extracted with ethyl acetate (3×60 mL), washed with brine solution (60 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (100-200 mesh; using 90% ethyl acetate in hexanes) to obtain 1-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-1-(pyridin-4-yl)ethanol as off-white solid (combined yield for 2 batches: 0.051 g, 4% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.58 (s, 2H), 7.99 (t, 2H), 7.48 (d, 2H), 7.04 (d, 2H), 6.98 (s, 1H), 1.94 (s, 3H); LC-MS m/z calculated for [M+H]+ 286.09, found 286.08.

1. stirringstirred for 2 h
2. customThe reaction mixture was quenched with saturated NH4Cl solution (50 mL)
3. extractionextracted with ethyl acetate (3×60 mL)
4. washwashed with brine solution (60 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by silica gel column chromatography (100-200 mesh; using 90% ethyl acetate in hexanes)
8. customto obtain

ORD record

ord-c6aa839c1f464728b02a52d8929ae71b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2