Triethylamine → 2-Bromo-6-(prop-1-en-2-yl)pyridine

To a solution of 2-(6-bromopyridin-2-yl)propan-2-ol (Example 2, Step 1) (2.44 g, 11.29 mmol) and methansulfonic anhydride (5.90 g, 33.9 mmol) in dichloromethane (35 mL) was added triethylamine (6.26 mL, 45.2 mmol). After three hours, the reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (25 mL) and brine (2×25 mL), dried over sodium sulfate, filtered, and concentrated. The resulting yellow liquid was purified by silica gel chromatography (2-20% ethyl acetate/hexanes) to afford the title compound.

1. customthe reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
2. customThe layers were separated
3. washthe organic layer was washed with saturated aqueous sodium bicarbonate (25 mL) and brine (2×25 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting yellow liquid was purified by silica gel chromatography (2-20% ethyl acetate/hexanes)

ORD record

ord-9bccd4730bd841b88063d3b4e431f524

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2