Dimethylformamide → 1589541-54-7

Temperature

0 °C

To a stirred solution of diisopropylethylamine (7.4 mL, 53.2 mmol) in THF was added n-BuLi (18.8 mL, 47.1 mmol, 2.5 M solution in hexanes) at −78° C., and allowed to stir at 0° C. of 30 minutes. The reaction mixture was again cooled to −78° C. and a solution compound tert-butyl(4,6-dichloropyridin-2-yl)carbamate (4.0 g, 15.2 mmol) in THF (20.0 mL) was added dropwise and stirred for 1 h at the same temperature. After 1 h, DMF (8.08 g, 36.7 mmol) was added at the same temperature and stirred for 30 minutes. After confirming the completion of starting material by TLC, the reaction mixture was quenched with saturated ammonium chloride solution extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure to get crude product which was purified by column chromatography (hexanes:ethyl acetate=4:1) to afford product. 1H NMR (ppm, 400 MHz, DMSO-d6): δ 10.95 (s, 1H), 10.22 (s, 1H), 7.95 (s, 1H), 1.47 (s, 9H).

1. temperatureThe reaction mixture was again cooled to −78° C.
2. stirringstirred for 1 h at the same temperature
3. waitAfter 1 h
4. stirringstirred for 30 minutes
5. customthe reaction mixture was quenched with saturated ammonium chloride solution
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto get crude product which
12. customwas purified by column chromatography (hexanes:ethyl acetate=4:1)
13. customto afford product

ORD record

ord-f0f7b6a242ec4dbea051358d6c4a15c0

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233979B2