Pyrrolidine → 1-(4-(4-(5-Chloro-4-(7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

_pyrrolidine (0.019 mL, 0.22 mmol)_ _was added to a suspension of_ _1-(4-(4-(5-chloro-4-(7-chloroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanone (104 mg, 0.20 mmol)_ _ in __dioxane (3.5 mL)_ _, followed by_ _sodium 2-methylpropan-2-olate (58.5 mg, 0.61 mmol)_ _, the mixture was degassed by bubbling N2 through , then __2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (3.79 mg, 6.09 µmol)_ _and_ _TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (2.79 mg, 3.04 µmol)_ _were added ._ _The orange suspension was stirred at _ _95 °C_ _for 2 hours under nitrogen atmosphere : no reaction observed_ _The same quantities of Binap and Pd2dba3 were added : 2 hours later ( no reaction ), _ _pyrrolidine (0.085 mL, 1.01 mmol)_ _was added and the yellow orange mixture was heated at 100°C overnight....no reaction_ _Water ( 1ml) was added , solution, and the heating was continued : mass pick 548, 549 appeared ( trce ? under SM pick ,Uplc, lcms2 acid conditions , trace of product) _ _An activated batch of Xantphos /Pd2dba3 ( 1.5/1 Pd ) was prepared and added and the heating continued no evolution_ _Not progressed isolation/recovery later_ _ _ _ _

Provenance & Evidence