Hydrogen Bromide → HCID 68410544, compound

6-Methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-4-ol (1.2 g) prepared in Reference Example 6 was dissolved in 60 mL of acetic acid, a solution of 2.72 g of bromine in 10 mL of acetic acid was added thereto by dropping, then 0.1 mL of 33% solution of hydrogen bromide in acetic acid solution was added thereto and the mixture was stirred for 3 hours at room temperature. To the reaction solution was added 10 mL of 10% aqueous solution of sodium thiosulfate and then the reaction solution was concentrated in vacuo to evaporate acetic acid. The residue was made basic by addition of 25% aqueous ammonia with cooling followed by extracting with ethyl acetate. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.74 g of the objective compound.

1. concentrationthe reaction solution was concentrated in vacuo
2. customto evaporate acetic acid
3. additionThe residue was made basic by addition of 25% aqueous ammonia
4. temperaturewith cooling
5. extractionby extracting with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
8. customthe solvent was evaporated
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-6290116160b84ecaa6aa405f8bba3ce3

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217031B2