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 conc 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-Eintrag

ord-a7d614d15578453aac23ead409ba94cc

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07989461B2