Water → 5-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

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Reaction Conditions

Reaction Steps

5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester (8.7 g, 29 mmol) was dissolved in toluene (85 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (1.2 g, 1.4 mmol), 4-chlorophenylboronic acid (4.9 g, 29 mmol) and sodium carbonate solution (2M, 30 mL). This mixture was heated to 90° C. for 1.5 h and cooled to room temperature. Water (150 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3) to give the title compound (5.3 g) as a pinkish solid; MS (ISP) 322.1 (M+H)+.

Provenance & Evidence