2-Bromomesitylene → Tert-butyl(2-(2-methoxyquinolin-3-yl)-2-oxoethyl)carbamate

Temperature

-78 °C

To a solution of mesityl bromide (4 eq.) in THF (1.7 M) cooled to −78° C. was added a solution of tBuLi in THF (8 eq., 1.7 M) dropwise. The mixture was left stirring at −78° C. for 1 h. Mixture was then allowed to reach 0° C. and a solution of 2-methoxyquinoline (3 eq.) in THF (0.32 M) was added dropwise over 10 min. The resulting mixture was aged at 0° C. for 1 h, then cooled to −78° C. and added dropwise with a solution of tert-butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (1 eq.) in THF (0.22 M). The reaction mixture was stirred at −78° C. for 30 min, then left at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with sat. aq. NaHCO3, dried over Na2SO4, and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc). Pooled fractions were concentrated under vacuum to give the title compound. MS (ES+) C17H20N2O4: 317 (M+H)+.

1. waitThe mixture was left
2. customto reach 0° C.
3. waitThe resulting mixture was aged at 0° C. for 1 h
4. temperaturecooled to −78° C.
5. stirringThe reaction mixture was stirred at −78° C. for 30 min
6. waitleft at room temperature overnight
7. washwashed with sat. aq. NaHCO3
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe resulting crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc)
11. concentrationPooled fractions were concentrated under vacuum

ORD record

ord-c5a5a608d3214263989bbc6a9921356a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365541B2