Toluene → propane-1-sulfonic acid(2,4-difluoro-3-[5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbony]-phenyl)-amide

Participants

Reaction Conditions

Reaction Steps

Into a microwave vial, propane-1-sulfonic acid {3-[5-bromo-1-(2,6-dichloro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide (11, 0.100 g, 0.158 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (12, 0.080 g, 0.33 mmol) and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.07 g, 0.086 mmol, 1:1 complex with dichloromethane) are combined with 2.0 mL of toluene and 2.0 mL of ethanol. The mixture is stirred for 5 minutes, then potassium carbonate (0.475 mL, 1.0 M aqueous) is added and the reaction heated at 110° C. for 60 minutes in a microwave, followed by 140° C. for 45 minutes. The reaction is added to silica and the solvents are removed under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate (with 2% acetic acid):hexanes. Appropriate fractions are combined and concentrated under vacuum, then washed with acetonitrile to provide the desired compound (P-0001). MS (ESI) [M+H+]+=496.0.

Provenance & Evidence