Methanol → N-(3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To N-(3-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.59 g, 0.98 mmol) in THF/IPA (1 mL/3 mL) was added trifluorovinylpotassium borate (0.20 g, 1.5 mmol), triethylamine (0.20 g, 2.0 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.080 g, 0.098 mmol). The reaction mixture was heated at 86° C. and stirred for 5 hours. The reaction mixture was cooled to ambient temperature, concentrated under reduced pressure, and triturated with Et2O (30 mL) to give crude vinyl product, to which palladium hydroxide on carbon (20% wt, 0.27 mmol) and MeOH (20 mL) was added. The system was purged with N2 three times and a H2 balloon was applied to the system for 2 hours. The reaction mixture was filtered through Celite, washed with MeOH (20 mL), and concentrated to give the product (0.32 g). MS (ES+APCI) m/z=506 (M+H).

Provenance & Evidence