Methanol → HCID 19799247, compound

Temperature

130 °C

Cu(OAc)2 (9.69 g, 53.39 mmol) was added to a stirred solution of 4-(4-fluorophenylamino)-5,6-dihydropyridin-2(1H)-one (I-59e: 5 g, 24.27 mmol) and Pd(OAc)2 (490 mg, 2.18 mmol) in DMF (96 mL) under argon atmosphere and the resulting reaction mass was heated at 130° C. for 2 hours. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was cooled to room temperature and filtered through a celite bed. The filtrate was partitioned between water and ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 2.2 g of the product (44.7% yield).

1. customthe resulting reaction mass
2. temperatureThe reaction mass was cooled to room temperature
3. filtrationfiltered through a celite bed
4. customThe filtrate was partitioned between water and ethyl acetate
5. washThe organic layer was washed with water, brine solution
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customto afford the crude product
9. customPurification by column chromatography on silica gel (1% methanol in DCM)

ORD record

ord-87dc5235a26b48fc8534067d6be46690

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946260B2