Potassium Carbonate → 1-((4-(4-Chlorophenyl)thiazol-2-yl)methyl)pyrrolidin-2-one

Temperature

97.5 °C

(4-chlorophenyl) boronic acid (0.22 g, 1.42 mmol) and potassium carbonate (0.41 g, 2.97 mmol) were added to a solution of 1-((4-bromothiazol-2-yl)methyl)pyrrolidin-2-one (Step-1 of Compound 103, 0.31 g, 1.18 mmol) in a mixture of toluene:ethanol (5:15 ml) in a tube at 25° C. Nitrogen gas was bubbled through the reaction mixture for 15 minutes. Tetrakis(triphenylphosphine)(0)palladium (0.07 g, 0.06 mmol) was then added to the reaction mixture under nitrogen atmosphere and the tube was sealed. The reaction mixture was heated at 95-100° C. for lhr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite. The celite cake was washed with ethanol (20 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.3 g, 86.6%).

1. customat 25° C
2. customNitrogen gas was bubbled through the reaction mixture for 15 minutes
3. customthe tube was sealed
4. temperatureThe reaction mixture was then cooled to 25° C.
5. filtrationfiltered through celite
6. washThe celite cake was washed with ethanol (20 ml)
7. concentrationThe combined filtrate was concentrated under reduced pressure
8. customto obtain a crude product, which
9. customwas then purified by column chromatography

ORD record

ord-a97c1b8094254b22a7901fc5afea14ec

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388196B2