Water → HCID 66665461, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1-{4-[3-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester [prepared in a manner analogous to that described in Int 11-0; 100% yield assumed] (0.29 mmol) in DMF (3 mL) was added 2-bromopyridine (0.034 mL, 0.32 mmol, 1.1 equiv) and dioxane (1.2 mL). The resulting solution was placed under an argon atmosphere, then, [1,1-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) CH2Cl2 complex (24 mg, 0.03 mmol, 10 mol %) and an aqueous 1 N NaOH solution (0.9 mL, 1.84 mmol, 6.3 equiv) were added. The resulting mixture was heated at 140° C. for 1 h in a microwave apparatus. The resulting mixture was added to water (15 mL). The resulting mixture was extracted with EtOAc (3×25 mL), dried (Na2SO4 anh), and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 10 g SNAP cartridge: 100% hexane for 2 min., gradient to 70% hexane/30% EtOAc over 1 min., 70% hexane/30% EtOAc for 3 min., gradient to 50% hexane/50% EtOAc over 1.5 min., 50% hexane/50% EtOAc for 2.5 min., gradient to 100% EtOAc over 1 min., 100% EtOAc for 9.6 min,) to give {1-[4-(3-phenyl-7-pyridin-2-yl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (85 mg, 54% two steps):

Provenance & Evidence