Ammonium Chloride → HCID 82374292, compound

To a mixture of ethyl 3-methylthieno[3,2-c]pyridine-2-carboxylate (3.40 g) synthesized above, calcium chloride (3.42 g), ethanol (30 mL) and tetrahydrofuran (30 mL) was added sodium borohydride (2.33 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a pale-yellow oil. To a solution (60 mL) of the obtained oil in tetrahydrofuran was added active manganese dioxide (14.4 g) and the mixture was stirred at 50° C. overnight. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (1.54 g, 56%) as a pale-brown solid.

1. customto quench
2. customthe reaction
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a pale-yellow oil
8. stirringthe mixture was stirred at 50° C. overnight
9. filtrationManganese dioxide was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. washThe residue was washed with diisopropyl ether

ORD record

ord-894f11bbab7d46948dd15407590e9df6

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2