Dichloromethane → HCID 117858280, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.8 g (9.24 mmol, 73% purity) of 4-bromo-2-[(2,6-difluorobenzyl)oxy]pyridine (Example 145A) in 54 ml of 1,4-dioxane and 13 ml of water was degassed under argon for 10 minutes. The solution was admixed with 9.04 g (27.73 mmol) of caesium carbonate, 0.82 g (11.09 mmol) of ethylboronic acid (CAS: 4433-63-0) and 0.75 g (0.924 mmol) of (1,1)-bis(diphenylphosphino)ferrocenedichloropalladium(II) complex with dichloromethane (CAS: 95464-05-4). The reaction vessel was closed and the contents were stirred at 100° C. for 18 hours. The solvent was evaporated off and the residue was partitioned between water and ethyl acetate. The organic phase was removed and concentrated under reduced pressure. The residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane/ethyl acetate, gradient 0% to 5%), which gave 1.38 g (41% yield, 69% purity) of product.

Provenance & Evidence