Heptane → 5-(4-Fluorophenyl)-6-cyclopropylmethoxy-nicotinic acid

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Reaction Conditions

Reaction Steps

5-Bromo-6-cyclopropylmethoxy-nicotinic acid (2.28 g, 8 mmol) was dissolved in a mixture of toluene (40 mL) and dimethylformamide (4 mL). To this solution was added [4-fluoro-phenyl]-boronic acid (1.2 g, 8 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]-dichloropalladium(II) dichloro-methane complex (307 mg), and 2 N sodium carbonate solution (33 mL). The whole mixture was heated with stirring at 90° C. for 4 h, cooled to room temperature and filtered. Phases were separated; the organic phase was discarded and the water phase was acidified with 1 N hydrochloric acid (pH 2) and extracted with ethylacetate. Etylacetate phases were pooled, dried with Na2SO4 and filtered over a small silica gel pad (20 g). The solvent was removed to yield a solid which was stirred with heptane (200 mL), filtered, washed with heptane and dried to yield 1.77 g of the title compound as beige solid, MS (ISP) 286.0 (M−H)−.

Provenance & Evidence