3-(2-THIENYL)PYRIDINE synthesis

Yield: 78%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in 1,4-dioxane;water at 80; for 24 h;Reflux;Suzuki-Miyaura coupling;

Steps:

4.3. General procedure for Suzuki-Miyaura cross-coupling reaction to obtain TPy compounds 3a-c through pathway B
General procedure: A mixture of pyridin-3-yl boronic acid 4a,b (2.00 equiv), halothiophene 5a-c (1.00 equiv), tetrakis(triphenylphosphine) palladium(0) (5% mol) and aq Na₂CO₃ (2.50 equiv) in 1,4-dioxane was heated at 80 °C for 1 h then under reflux until the complete consumption of aryl halide (as monitored by TLC) (23 h). The reaction mixture was concentrated and extracted with ethyl acetate. Organic layer was dried over MgSO₄ and concentrated. The residue was purified on silica gel column chromatography (cyclohexane/ethyl acetate: 7/3) to afford compounds 3a-c.

References:

De Giorgi, Marcella;Voisin-Chiret, Anne Sophie;Sopkova-De Oliveira Santos, Jana;Corbo, Filomena;Franchini, Carlo;Rault, Sylvain [Tetrahedron,2011,vol. 67,# 34,p. 6145 - 6154] Location in patent:experimental part