3,4-Dimethylaniline → N-(3,4-dimethylphenyl)-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridin-4-amine

Into a 100-mL 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3,4-dimethylbenzenamine (2 g, 16.53 mmol, 4.98 equiv) in N,N-dimethylformamide (50 mL), and sodium hydride (660 mg, 16.50 mmol, 4.97 equiv, 60%). The resulting solution was stirred for 1 h at room temperature. To this was added 4-fluoro-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine (1 g, 3.32 mmol, 1.00 equiv). The resulting solution stirred for an additional 1 h at 50-80° C. in an oil bath. The reaction mixture was cooled. The reaction was then quenched with 150 mL of H2O. The resulting solution was extracted with 3×60 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×60 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate:petroleum ether (1:1). The product was obtained as 500 mg (37%) of a yellow solid.

1. customInto a 100-mL 3-necked round bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution stirred for an additional 1 h at 50-80° C. in an oil bath
4. temperatureThe reaction mixture was cooled
5. customThe reaction was then quenched with 150 mL of H2O
6. extractionThe resulting solution was extracted with 3×60 mL of ethyl acetate
7. washThe resulting mixture was washed with 1×60 mL of brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under vacuum
10. washeluted with ethyl acetate:petroleum ether (1:1)

ORD record

ord-02328566431241eb91eba35fdbab208e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916569B2