6-[4-(TrifluoroMethoxy)phenyl]-3-pyridinecarbaldehyde synthesis

Yield:851069-97-1 72%

Reaction Conditions:

with potassium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in tetrahydrofuran;water at 80; for 24 h;Inert atmosphere;

Steps:

1

Procedure 3[00164] Potassium carbonate (12.2 g, 88.27 mmol) in distilled water (30 mL) was added anhydrous tetrahydrofuran (80 mL) under Nitrogen. Carboxaldehyde (5.5 g, 29.57 mmol) was added followed by tetrakis(triphenylphosphine)palladium (0) (2.73 g, 2.36 mmol). The mixture was left stirring at room temperature for 5 min under N₂. Boronic acid (6.77 g, 32.88 mmol) was added. The resulting mixture was heated to 80°C for 24 h (followed by tic). The reaction was cooled to room temperature. It was extracted with ethyl acetate (x 3), washed with brine, dried over MgS0₄, filtered and concentrated to oil. The crude product was purified by column chromatography using 10% ethyl acetate in hexane to give the title compound as a white solid.

References:

WO2012/69856,2012,A1 Location in patent:Page/Page column 52; 54-55