Cesium carbonate → Methyl 4-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-3,5-dimethylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(2-chloroquinoline-4-carboxamido)-3,5-dimethylbenzoate, (0.50 g, 0.00135 mol), tert-butyl-dimethyl-(4-piperidyloxy)silane (0.32 g, 0.0015 mol, see preparation 3) and Cs2CO3 (1.77 g, 0.0054 mol) in 1,4-dioxane (5 ml) is added Pd2(dba)3 (0.124 g, 0.000135 mol) followed by S-Phos (0.060 g, 0.000135 mol). The reaction mixture is purged with nitrogen for 5 minutes and then stirred at 80° C. After 4 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The organic layers are combined and dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (0.21 g, 28%). Mass spectrum (m/z): 548.2 (M+1).

Provenance & Evidence