Methyl iodide → HCID 57441134, compound

Participants

Reaction Steps

To a degassed solution of 10.48 g (50.9 mmol) of 3,5-dichloro-pyridine-2-carboxylic acid methyl ester [prepared in analogy to the procedure described for the preparation of intermediate 5A from 3,5-dichloro-pyridine-2-carboxylic acid and iodomethane, potassium carbonate in DMF] in 400 ml of dimethoxyethane were added 14.49 g (76.3 mmol) of 3-(trifluoromethyl)phenyl boronic acid and 49.73 g (152.6 mmol) of caesium carbonate. While stirring, 0.77 g (1.50 mmol) of [(t-Bu)2P(OH)]2PdCl2 (POPd) was added and the reaction mixture was stirred at reflux for 7 hours. It was then cooled down to RT, poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 98:2 to 1:1) to give 3.22 g (20%) of 3-chloro-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester as light yellow oil; [MS: 316.0 (MH+, 1Cl)] and 2.80 g (12.9%) of 3,5-bis-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester as light yellow solid; [MS: 426.1 (MH+)] and 3.21 g (20.0%) of 5-chloro-3-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester as light yellow oil. [MS: 316.0 (MH+, 1Cl)].

Provenance & Evidence