Potassium Phosphate, Tribasic → 3-Cyclopropyl-3-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile (Preparation M; 0.050 g, 0.16 mmol), 1-(oxetan-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Table 2, compound f; 0.078 g, 0.21 mmol), and potassium phosphate (0.24 mL, 0.48 mmol) was added 2 mL of dioxane and argon was bubbled through for 5 minutes before dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.015 g, 0.032 mmol) and tris(dibenzylideneacetone)dipalladium (0.015 g, 0.016 mmol) were added. The reaction was fitted with a septum and argon was bubbled through for 10 minutes before it was sealed and then heated to 75° C. for 2 hours. The reaction mixture was diluted with dichloromethane and loaded directly onto a silica gel column pre-wetted and eluted with ethyl acetate containing 0.5% ammonium hydroxide to afford the title compound (0.034 g, 0.081 mmol, 50% yield). MS (apci) m/z=401.2 (M+H).

Provenance & Evidence