Hydrochloric Acid → 2-Bromo-6-(1-pyrrolidin-1-ylethyl)pyridine

Temperature

0 °C

A solution of 1-(6-bromopyridin-2-yl)ethanol (Example 3, Step 1) (0.5 g, 2.48 mmol) in tetrahydrofuran (4 mL) at 0° C. was charged with triethyl amine (1.04 mL, 7.42 mmol), and then a solution of methanesulfonic anhydride (0.56 g, 3.22 mmol) in tetrahydrofuran (6 mL) added over 30 minutes. The reaction mixture was stirred at 0° C. for 2 hrs and then pyrrolidine (0.21 mL, 2.48 mmol) was added and the mixture was warmed to room temperature. After sixteen days the reaction mixture was poured into aqueous hydrogen chloride (1 M, 10 mL) and dichloromethane (10 mL) The layers were separated and the organic layer was extracted with aqueous hydrogen chloride (1 M, 10 mL). The combined aqueous layers were neutralized with aqueous sodium hydroxide (2 M) until pH=10 and then extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the title compound.

1. temperaturethe mixture was warmed to room temperature
2. customwere separated
3. extractionthe organic layer was extracted with aqueous hydrogen chloride (1 M, 10 mL)
4. extractionextracted with dichloromethane (3×20 mL)
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-79795668c5194202a6f2c4be24b8dbd5

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2