Cesium carbonate → Methyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(pyrrolidin-3-ylmethoxy)silane (0.4 g, 1.99 mmol) and Cs2CO3 (1.2 g, 3.99 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 20% EtOAc in hexane to afford the title compound as a brown semi solid (0.36 g, 53%). Mass spectrum (m/z): 511.2 (M+1).

Provenance & Evidence