Acetonitrile → 3-[3-(2-Methyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

Participants

Reaction Steps

The title compound was prepared from 3-(2-methyl-pyridin-4-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-carboxyphenylboronic acid (7.13 g, 43.0 mmol) and 4-bromo-2-methylpyridine [Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] (7.40 g, 43.0 mmol) in acetonitrile (215 ml) and 0.4M Na2CO3-solution (215 ml) was degassed and Pd(Ph3P)4 (5.0 g, 0.43 mmol) was added. The reaction mixture was refluxed for 18 h and evaporated to dryness [Synlett 2000 (6), 829-831]. The residue was suspended in MeOH (215 ml), SOCl2 (15.6 ml, 215 mmol) was added dropwise at RT and the reaction mixture was refluxed for 4h. Aqueous work-up and further purification by column chromatography as described in example K4] (10.1 g, 44.4 mmol) by treatment with tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (9.50 g, 69%).

Provenance & Evidence