4-Chloroaniline → HCID 59570661, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of give [5-bromo-3-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-carbamic acid tert-butyl ester (511 mg, 1.25 mmol), 4-chloroaniline (223 mg, 1.75 mmol) and cesium carbonate (822 mg, 2.5 mmol) in dioxane (35 mL) was degassed with argon for 15 min. Tris(dibenzylideneaceton)dipalladium (0) 29 mg, 0.03 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (57 mg, 0.1 mmol) were added followed by degassing for 5 min. The reaction mixture was heated to 120° C. for overnight. Ethyl acetate, water and brine were added and the phases were separated. The aqueous phase was extracted with ethyl acetate (5×50 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo. The crude product purified by flash chromatography (ethyl acetate/heptane as eluent) to give [5-(4-chloro-phenylamino)-3-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-carbamic acid tert-butyl ester (225 mg, 43%) as an yellow solid.

Provenance & Evidence