Triethylamine → 7-fluoro-3,4-dihydro-1,5-naphthyridin-2(1H)-one

Temperature

60 °C

To a suspension of 9.1 g of butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate and 0.9 g of 10% palladium carbon in 30 mL of methanol, 4 mL of formic acid was added, and 15 mL of triethylamine was added dropwise thereto under ice cooling. The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, insoluble matter was filtered out, and the filter residue was washed using 30 mL of toluene. The filtrate and the wash liquid were combined and the solvent was evaporated under reduced pressure. To the obtained residue, 30 mL of toluene was added, the mixture was stirred at 100° C. for 2 hours and 30 minutes. To the reaction mixture, 30 mL of water was added dropwise at 45° C. and the mixture was cooled to 5° C. The solid product was obtained by filtration and washed in the order of water and toluene to give 5.7 g of 7-fluoro-3,4-dihydro-1,5-naphthyridin-2(1H)-one as a white solid.

1. additionwas added
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationinsoluble matter was filtered out
4. washthe filter residue was washed
5. customthe solvent was evaporated under reduced pressure
6. additionTo the obtained residue, 30 mL of toluene was added
7. stirringthe mixture was stirred at 100° C. for 2 hours and 30 minutes
8. additionTo the reaction mixture, 30 mL of water was added dropwise at 45° C.
9. temperaturethe mixture was cooled to 5° C
10. customThe solid product was obtained by filtration
11. washwashed in the order of water and toluene

ORD record

ord-156315db178d4ec6bdfd2a4daebbb072

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354426B2