Pyridine → HCID 4643451, compound

Temperature

45 °C

To a solution of methyl 3-aminothiophene-2-carboxylate (2.98 g; 11.7 mmol) in anhydrous dichloromethane (32 mL) were added pyridine (1.54 mL; 19.0 mmol) and 4-bromobenzenesulfonyl chloride (1.49 g; 9.5 mmol) in one portion. The reaction mixture was heated at 45° C. for 71 hours, allowed to cool to room temperature, and then diluted with dichloromethane (100 mL). The resulting mixture was successively washed with aqueous hydrochloric acid (50 mL; 2N) and aqueous saturated sodium chloride (50 mL), dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to yield an off-white solid. The crude product was dissolved in dichloromethane (100 mL) and treated with aqueous sodium hydroxide (60 mL; 2N) resulting in a white precipitation. The white solid was isolated by filtration and washed with dichloromethane (50 mL). The white solid was then acidified with aqueous hydrochloric acid (60 mL; 6N) and extracted with dichloromethane (2×100 mL). The organic extracts were combined, washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title compound as a pale yellow solid (2.53 g).

1. temperatureto cool to room temperature
2. washThe resulting mixture was successively washed with aqueous hydrochloric acid (50 mL; 2N) and aqueous saturated sodium chloride (50 mL)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customto yield an off-white solid
7. customresulting in a white precipitation
8. customThe white solid was isolated by filtration
9. washwashed with dichloromethane (50 mL)
10. extractionextracted with dichloromethane (2×100 mL)
11. washwashed with aqueous saturated sodium chloride
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure

ORD record

ord-adf27596b72d482dbb30ab27d20ec786

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178699B2