Ammonium Chloride → Cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methanone

To a solution (30 mL) of 3-methylthieno[2,3-c]pyridine-2-carbaldehyde (1.39 g) synthesized above in tetrahydrofuran was added a 1.0M solution (15.7 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1.5 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give a pale-yellow solid. To a mixture of the obtained solid, 4-methylmorpholine N-oxide (680 mg) and acetonitrile (20 mL) was added tetrapropylammonium perruthenate (113 mg), and the mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane) to give the title object compound (628 mg, 31%) as a colorless oil.

1. customto quench
2. customthe reaction, tetrahydrofuran
3. customwas evaporated in an evaporator
4. extractionthe residue was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)
9. customto give a pale-yellow solid
10. stirringthe mixture was stirred at room temperature for 1 hr
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (0-40% ethyl acetate/hexane)

ORD record

ord-7368ebd04c6d4eb9a3fc180002ba9fce

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2