Phenylsilane → HCID 178472484, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl trans-4-{[6-chloro-5-(3-cyano-4-fluorophenyl)-1-(prop-2-en-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy}cyclohexanecarboxylate (980 mg, 2.029 mmol) in DMSO (4 mL) was added 1,1′-bis(diphenylphosphinoferrocene-Palladium (II) dichloride dichloromethane complex (148 mg, 0.203 mmol) followed by phenylsilane (220 mg, 2.029 mmol). The reaction was heated at 90° C. for 1 h. The reaction was then cooled, quenched with citric acid (10% w/v, 5 mL) and then extracted with EtOAc (2×10 mL). The organic layers were collected, dried and then concentrated in vacuo. The residue was purified via flash chromatography (40 g column, 40 mL/min flow, 0-100% EtOAc/hexane to afford ethyl trans-4-{[6-chloro-5-(3-cyano-4-fluorophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy}-cyclohexanecarboxylate as a yellow foam.

Provenance & Evidence