Potassium Carbonate → HCID 178441171, compound

Participants

Reaction Steps

To a round bottomed flask, add 1-(4-bromo-phenyl)-3-(5-tert-butyl-2H-pyrazol-3-yl)-urea (0.41 g, 1.2 mmol), tricyclohexylphosphine (24 mg, 0.07 equiv.), potassium acetate (0.36 g, 3 equiv.), bis(pinacolato)diboron (0.34 g, 1.1 equiv.) and DMSO (5 mL). Deoxygenate this mixture thoroughly with N2 then add tris(dibenzylideneacetone)-di-palladium (0) (33 mg, 0.03 equiv.) and heat to 100° C. overnight. Dilute the reaction with EtOAc and wash with water then saturated aqueous saturated sodium chloride. Pass the organic layer thru a Celite® plug then dry over magnesium sulfate, filter and concentrate to a residue (0.72 g). MS (ES), m/z 385.4 (M+1) is present. Add to this residue 3-iodo-7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridine (0.25 g, 0.62 mmol), potassium carbonate (0.26 g, 1.86 mmol), dioxane (10 mL), and water (5 mL). Deoxygenate this mixture thoroughly with N2 then add dichloro-bis(triphenylphosphine) palladium (II) (13 mg, 0.03 equiv.) and reflux the reaction overnight under N2. Concentrate the reaction to dryness and slurry in acetone and filter to remove insolubles. Concentrate the filtrate then purify by silica column (1:1 Hex:EtOAc to 1:2 Hex:EtOAc to EtOAc to 5% MeOH:DCM) to give crude product. Triturate from DCM to give a pale yellow solid (0.059 g, 18%). MS (ES), m/z 529 (M+1).

Provenance & Evidence