2-Bromo-3-methylpyridine → 3-Methyl-2,2'-bipyridine

To a flask were added 1.0 g 2-bromo-3-methylpyridine and 10 ml of dry tetrahydrofuran. The solution was purged with nitrogen and 34 mg tetrakis(triphenylphosphine)palladium was added followed by 17.4 ml of a 0.5M solution of 2-pyridylzinc bromide in tetrahydrofuran. The mixture was stirred at 22 C for 24 hours, then 40 C for 72 hours. The mixture was poured into a solution of 5 g EDTA, 2 g sodium carbonate and 40 ml water. The product was extracted twice with diethylether, washed with water and dried over sodium sulfate. Following filtration and solvent removal, the product was purified by silica gel chromatography using 48% ethyl acetate, 48% hexane and 4% methanol. A slightly yellow oil remained 0.38 g.

1. customThe solution was purged with nitrogen and 34 mg tetrakis(triphenylphosphine)palladium
2. additionwas added
3. wait40 C for 72 hours
4. additionThe mixture was poured into a solution of 5 g EDTA, 2 g sodium carbonate and 40 ml water
5. extractionThe product was extracted twice with diethylether
6. washwashed with water
7. dry with materialdried over sodium sulfate
8. filtrationfiltration and solvent removal
9. customthe product was purified by silica gel chromatography

ORD record

ord-170f2b21312e416b9c68ff8484029d16

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09011734B2