Pyridine → HCID 57929916, compound

1-(2,4-Difluorophenyl)but-2-yn-1-one (3.95 g, 21.93 mmol, prepared as described in WO 2000008002, Intermediate #39) was dissolved in MeOH (60 mL) then pyridine (6 mL) and O-methylhydroxylamine hydrochloride (3.66 g, 43.9 mmol) were added. The mixture was stirred for about 2 min until a solution was obtained then sodium sulfate (6.23 g, 43.9 mmol) was added. The mixture was stirred overnight at ambient temperature then the mixture was diluted with water (150 mL) and extracted with ethyl acetate (3×50 mL). The combined organic solutions were extracted with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to an oil. The material was purified by flash chromatography silica gel with heptane/ethyl acetate (85:15) as an eluent to give the title compound: (2.29 g, 50%): LC/MS (Table 1, Method g) Rt=2.58 min; MS m/z: 210.0 (M+H)+.

1. customwas obtained
2. stirringThe mixture was stirred overnight at ambient temperature
3. extractionextracted with ethyl acetate (3×50 mL)
4. extractionThe combined organic solutions were extracted with brine (50 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure to an oil
8. customThe material was purified by flash chromatography silica gel with heptane/ethyl acetate (85:15) as an eluent

ORD record

ord-ca8739674ee24e6790f1325e7700d89d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188083B2