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

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence