Hydrochloric Acid → (2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(thien-2-yl)methanone

Temperature

-78 °C

To a solution of 2-bromothiophene (2.7 g, 16 mmol) in dimethyl ether (30 ml) was added dropwise 1.6 M solution (8.9 ml) of n-butyllithium in n-hexane at −78° C. The reaction mixture was stirred at −78° C. for 30 min. and a solution of 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (2.0 g, 6.4 mmol) in tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min. and 0.1N hydrochloric acid was added. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(thien-2-yl)methanone (0.98 g, yield 46%) as a yellow oil.

1. stirringThe reaction mixture was stirred at −78° C. for 30 min.
2. extractionThe mixture was extracted with ethyl acetate
3. washthe extract was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography

ORD record

ord-3eb596bd4a8e4f0eaf363e5341800c21

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547710B2