3-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one → N-[3-(5-Amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

温度

95 °C

A 48-mL sealed tube equipped with a magnetic stirring bar was charged with 3-amino-5-bromo-1-methyl-1H-pyridin-2-one (4) (0.10 g, 0.50 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (0.24 g, 0.70 mmol), and Pd(PPh3)4 (0.030 g, 0.025 mmol) in DME (10 mL) and 1N Na2CO3 (5 mL). After the mixture was degassed for 15 min., it was heated at 95° C. for 16 h. Then, the reaction mixture was cooled to room temperature and poured into H2O (10 mL). To this was added dichloromethane and the phases were separated. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with H2O (5 mL) and brine (5 mL), dried (Na2SO4), and concentrated. The crude mixture was purified by column chromatography, gradient 0-10% MeOH in dichloromethane/ether (1/1), to afford 0.14 g (68%) of N-[3-(5-amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (5) as a solid.

1. customA 48-mL sealed tube
2. customequipped with a magnetic stirring bar
3. customAfter the mixture was degassed for 15 min.
4. temperatureThen, the reaction mixture was cooled to room temperature
5. additionpoured into H2O (10 mL)
6. additionTo this was added dichloromethane
7. customthe phases were separated
8. extractionThe aqueous layer was extracted with dichloromethane
9. washthe combined organic layers were washed with H2O (5 mL) and brine (5 mL)
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated
12. customThe crude mixture was purified by column chromatography, gradient 0-10% MeOH in dichloromethane/ether (1/1)

ORDレコード

ord-44488debdef744dbb1dce93dd9901593

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08058446B2