Potassium Acetate → 2-[2-Fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(5-isopropyl-4-methyl-thiazol-2-yl)-acetamide

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Reaction Steps

Combine 7-pyridin-4-yl-imidazo[1,2-a]pyridine (0.242 g, 1.24 mmol), 2-(4-Bromo-2-fluoro-phenyl)-N-(5-isopropyl-4-methyl-thiazol-2-yl)-acetamide (0.460 g, 1.24 mmol), and potassium acetate (0.243 g, 2.48 mmol) in DMSO (5 mL). De-gas the mixture with N2 for 10 minutes, then add dichlorobis(triphenylphosphine) palladium(II) (0.087 g, 0.124 mmol). Stir the reaction at 100° C. under N2 for 14 hours. Purify using an SCX cartridge (10 g VARIAN bond elut), eluting with 1:1 methanol:dichloromethane, then 1:1 2 M NH3 in methanol:dichloromethane. The latter is purified via reverse phase chromatography using a 25 cm by 50.8 mm (i.d.) column w/10 micron particles (MeCN/0.03% HCl H2O (5:95) to 100% MeCN; 30 minutes). Compound obtained is extracted with ethyl acetate versus 1 N NaOH. The organic layer is washed with aqueous saturated sodium chloride. Dry the resulting organics over magnesium sulfate, filter, and concentrate to afford product (0.068 g, 11%). MS(ES), m/z 486 (M+1).

Provenance & Evidence