2-(4-FLUOROPHENYL)NICOTINALDEHYDE synthesis

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 115; for 0.333333 h;Microwave vial;

Steps:

9.A

2-Bromonicotinaldehyde (250 mg, 1.34mmol), 4-fluorophenylboronic acid (226 mg, 1.61 mmol), dioxane (6.7 mL) and sodium bicarbonate (sat.) (6.7 mL) were added to a microwave vial. PdCl2(dppf) (49 mg, 0.067 mmol) was added. The mixture was sonicated and microwaved as a high absorber at 115°C for 20 minutes. Solvent was evaporated under vacuum to give a residue. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL) and filtered. The filtrate was transferred to a separatory funnel. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The organic layers were combined and washed with brine (25 rnL). The organics were dried over sodium sulfate and filtered. The solvent from the filtrate was evaporated under vacuum to give the title compound. The material was carried forward to the next step without further purification. MS [M+H] found 202.

References:

WO2010/129848,2010,A2 Location in patent:Page/Page column 26-27