Methyl iodide → 9-Bromo-8-methoxy-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one

Temperature

0 °C

To a stirred solution of diidopropylamine (85 μL, 0.6 mmol) in THF (2.5 mL) at −78° C. was added n-BuLi (2.5 M, 0.24 mL, 0.60 mmol) and the reaction mixture was stirred at 0° C. for 10 min then cooled to −78° C. A solution of 9-bromo-8-methoxy-6-methyl-5-((2-(trimethylsilyl)ethoxy)methyl)thieno[2,3-c]quinolin-4(5H)-one (0.23 g, 0.50 mmol) in THF (1 mL) was added dropwise and the reaction mixture was stirred at −78° C. for 30 min. Iodomethane (93 μL, 1.5 mmol) was added and the reaction mixture was stirred at −78° C. for 2 h and quenched by the addition of satd. aq. ammonium chloride and extracted with dichloromethane. The organics were dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by column chromatography (silica, heptane/ethyl acetate) to afford the desired product (0.13 g, 55%) as a white solid: ESI MS m/z 468 [C20H26BrNO3SSi+H]+.

1. temperaturethen cooled to −78° C
2. stirringthe reaction mixture was stirred at −78° C. for 30 min
3. stirringthe reaction mixture was stirred at −78° C. for 2 h
4. customquenched by the addition of satd
5. extractionaq. ammonium chloride and extracted with dichloromethane
6. dry with materialThe organics were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customthe residue was purified by column chromatography (silica, heptane/ethyl acetate)

ORD record

ord-e987a8338e084580a6a681c088d20f30

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962648B2