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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(2-chloroquinoline-4-carboxamido)-2,4-dimethylbenzoate (0.54 g, 0.00146 mol), tert-butyl-dimethyl-(4-piperidyloxy)silane (0.63 g, 0.00293 mol, see preparation 3) and Cs2CO3 (1.43 g, 0.0044 mol) in 1,4-dioxane (8 ml) is added Pd2(dba)3 (0.134 g, 0.000146 mol) followed by S-Phos (0.060 g, 0.000146 mol). The reaction mixture is purged with nitrogen for 5 minutes and then stirred at 80° C. After 16 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 as a black semi-solid (1.31 g, 60%, crude). Mass spectrum (m/z): 548.2 (M+1).

Provenance & Evidence