Hydrochloric Acid → 3-Bromo-2-methylthieno[2,3-c]pyridine

N-((4-bromo-5-methylthiophen-2-yl)methyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide (20 g, 45 mmol) was dissolved in dioxane (70 ml) and treated with cone HCl (70 ml). The reaction was heated to reflux and stirring continued overnight. The reaction was cooled down to RT, then to 0° C. and rendered neutral with 2N NaOH. The mixture was extracted with ethyl acetate. The organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes to give 3-bromo-2-methylthieno[2,3-c]pyridine (6.2 g, 61% yield) as an yellow solid. MS (M+H)+ 229

1. temperatureThe reaction was heated
2. temperatureto reflux
3. customto 0° C.
4. extractionThe mixture was extracted with ethyl acetate
5. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
6. dry with materialThe organic layer was then dried with sodium sulfate
7. custompurified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes

ORD record

ord-f8a1bf598ed144d1b799074b8b56587b

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440674B2