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

Temperature

-78 °C

To a solution of mesyl bromide (17.23 mmol) in 10 mL of THF cooled to −78° C. was added a 1.7 M THF solution of tBuLi (34.5 mmol) dropwise. The mixture was left stirring at −78° C. for 1 h. The mixture was then allowed to reach 0° C. and a solution of 2-methoxyquinoline (12.9 mmol) in THF (40 mL) was added dropwise over 10 min. The resulting mixture was aged at 0° C. for 1 h, cooled to −78° C. and added dropwise with a solution of tert-butyl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (4.31 mmol) in 20 mL of THF. The mixture was stirred at −78° C. for 30 min then left at room temperature over night. The mixture was diluted with DCM and washed with sat. aq. NaHCO3, dried (Na2SO4), concentrated under reduced pressure and the crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc). Pooled fractions were concentrated under vacuum to title product (1.01 g). MS (ES) C17H20N2O4 requires: 316.35, found: 317.

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 mixture was stirred at −78° C. for 30 min
6. waitthen left at room temperature over night
7. washwashed with sat. aq. NaHCO3
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated under reduced pressure
10. customthe crude product was purified by flash chromatography (SiO2, Petroleum ether/EtOAc, from 5% to 40% EtOAc)
11. concentrationPooled fractions were concentrated under vacuum to title product (1.01 g)

ORD record

ord-619a52425651405e81622260e8ff2656

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371295B2