Methanol → HCID 68410468, compound

To a solution of 4-(2-fluoropyridin-3-yl)-5-[(pyridin-2-yl)thio]thiophene-2-carbaldehyde (270 mg) in tetrahydrofuran (2 mL) were added 40% methylamine-methanol solution (0.9 mL) and methanol (2 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (3 mL), and sodium tetrahydroborate (222 mg) was added at 0° C. The mixture was stirred at room temperature for 1 day and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield 286 mg, yield quantitative).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in methanol (3 mL)
3. additionsodium tetrahydroborate (222 mg) was added at 0° C
4. stirringThe mixture was stirred at room temperature for 1 day
5. concentrationconcentrated under reduced pressure
6. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-b5661cb840e2489994e66cabd339e6ee

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334301B2