Sodium Carbonate → 1-[5-(7-Pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-pyridin-2-yl]-3-(m-trifluoromethyl-phenyl)-urea

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-bromopyridin-2-yl)-3-(m-trifluoromethylphenyl)-urea (0.520 g, 1.44 mmol, 1.0 eq.) in dioxane (12 mL), add bis(pinacolato)diboron (0.410 g, 1.59 mmol, 1.1 eq.), tricyclohexylphosphine (0.048 g, 12 mol %), potassium acetate (0.211 g, 1.5 eq.), and tris(dibenzylidineacetone)dipalladium (0) (0.066 g, 5 mmol %). Deoxygenate the reaction mixture and stir under nitrogen at 80° C. for approximately 16 h and cool to room temperature. Add 3-iodo-7-pyridin-4-yl-imidazo[1,2-a]pyridine (0.460 g, 1.44 mmol, 1.0 eq.), sodium carbonate solution (2 M, 3 mL) and tetralis(triphenylphosphine)palladium (0) (0.083 g, 5 mmol %). Deoxygenate the reaction mixture and stir at 80° C. for 6 hours, cool, then purify on a SCX cartridge (Varian) as in Example 115. Concentrate SCX-eluted materials and purify via silica gel flash chromatography employing a 0-4% gradient of methanol in dichloromethane to afford 0.450 g (0.99 mmol, 69%) of the title compound. MS (ES), m/z 475 (M+1).

Provenance & Evidence