5-Nitro-2-(4-vinylphenyl)pyridine synthesis

Yield:1422173-02-1 67%

Reaction Conditions:

with bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾;potassium carbonate in tetrahydrofuran;water at 100; for 0.5 h;Microwave irradiation;Inert atmosphere;Suzuki-Miyaura Coupling;

Steps:

N,N-Dimethyl-4'-vinylbiphenyl-4-amine 11a.

General procedure: 3 (75 mg , 0.50 mmol), 9h (100 mg, 0.50 mmol), bis[1,2-bis(diphenylphosphino)ethane]palladium(0) (5 mg, 0.005 mmol), potassium carbonate (166 mg, 1.20 mmol), THF (5 mL) and water (5 mL) were placed in a microwave vial, purged with nitrogen, sealed and stirred under microwave irradiation (power 100 W) at 100 oC for 30 min. The mixture was cooled to rt, diluted with EtOAc (20 mL) and filtered on Celite. The filtrate was washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to give 139 mg of a yellow solid. The crude product was purified by chromatography on silica gel, hexane/EtOAc 9:1, to give 70 mg of the pure expected product as a yellow solid in 63% yield (0.50 mmol scale).

References:

Baltus, Christine B.;Chuckowree, Irina S.;Press, Neil J.;Day, Iain J.;Coles, Simon J.;Tizzard, Graham J.;Spencer, John [Tetrahedron Letters,2013,vol. 54,# 10,p. 1211 - 1217] Location in patent:supporting information