Water → 2,4,6-Trimethyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

Temperature

-78 °C

To a solution of 1.05 g (2.23 mmol) of mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine in 20 ml of THF 7.60 ml (5.60 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The resulting mixture was heated to room temperature and then stirred for 10 min. Further on, 2 ml of water was added, and then the reaction mixture was poured into 50 ml of water. The crude product was extracted with 3×20 ml of ether. The organic extract was washed by 2×30 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 0.90 g (66%) of yellow oil. Anal. calc. for C39H37N3: C, 85.52; H, 6.81; N, 7.67. Found: C, 85.73; H, 6.98; N, 7.54. For 1H NMR (in CDCl3) see FIG. 2—Bottom spectrum.

1. temperatureThe resulting mixture was heated to room temperature
2. stirringstirred for 10 min
3. extractionThe crude product was extracted with 3×20 ml of ether
4. extractionThe organic extract
5. washwas washed by 2×30 ml of water
6. dry with materialdried over K2CO3
7. customevaporated to dryness
8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.)

ORD record

ord-afedf8f848be46a89d8365824fe7e2f4

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394902B2