Acetonitrile → 3-[3-(6-Cyano-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from 3-(6-cyano-pyridin-3-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-carboxyphenylboronic acid (2.08 g, 12.51 mmol) and 5-bromo-pyridine-2-carbonitrile [CAS-No. 97483-77-7] (2.08 g, 11.37 mmol) in acetonitrile (55 ml) and 0.4M Na2CO3-solution (55 ml) was degassed and Pd(Ph3P)4 (657 mg, 0.57 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 (300 ml), SOCl2 (2.61 ml, 36 mmol) was added dropwise at 23° C. and the reaction mixture was stirred at 23° C. for 3 days. Concentrated in vacuum to about 100 mL, diluted with EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown residue, which was purified by silica gel column chromatography with cyclohexane/EtOAc.] (1.38 g, 5.79 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as an orange oil (530 mg).

Provenance & Evidence