Water → 2-Bromo-6-(2-methoxyethyl)pyridine

A solution of sodium hydride (59 mg, 1.49 mmol) in tetrahydrofuran (2 ml) was cooled to 0° C. in an ice bath. 2-(6-Bromopyridin-2-yl)ethanol (Example 235 Step 3) (100 mg, 0.49 mmol) in tetrahydrofuran (2 ml) was added dropwise and the reaction was allowed to warm to room temperature. After 45 minutes at room temperature, the reaction was cooled to 0° C., followed by the addition of methyl iodide (0.09 ml, 1.49 mmol). The reaction was then allowed to warm to room temperature. Upon completion, the reaction was cooled to 0° C. and water was added dropwise. Ethyl acetate was then added and the layers were separated. The organic layer was then dried over sodium sulfate, filtered and concentrated. Purification of the crude residue by silica gel chromatography afforded the title compound.

1. temperaturethe reaction was cooled to 0° C.
2. temperatureto warm to room temperature
3. temperatureUpon completion, the reaction was cooled to 0° C.
4. customthe layers were separated
5. dry with materialThe organic layer was then dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification of the crude residue by silica gel chromatography

ORD record

ord-e2102422db514b3a8be8f55a7edb3112

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2