5-(Tributylstannyl)-1,3-thiazole → 3-Cyclopropyl-3-(4-(7-(thiazol-5-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; 0.020 g, 0.064 mmol), 5-(tributylstannyl)thiazole (0.029 g, 0.077 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0061 g, 0.013 mmol), and tris(dibenzylideneacetone)dipalladium (0.0059 g, 0.0064 mmol), evacuated and backfilled with argon, was added 1.5 mL of dioxane. Argon was bubbled through the reaction for 5 minutes and the flask was sealed and heated to 100° C. for 3 hours. The reaction mixture was loaded onto a silica gel column pre-wetted and eluted with ethyl acetate containing 0.5% ammonium hydroxide to afford the title compound (0.018 g, 0.050 mmol, 78% yield). MS (apci) m/z=362.1 (M+H).

Provenance & Evidence