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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(5-bromo-2-methylbenzamido)-3,5-dimethylbenzoate (0.5 g, 0.0013 mol), tert-butyl-dimethyl-(3-piperidylmethoxy)silane (0.45 g, 0.0019 mol, preparation 14) and Cs2CO3 (1.29 g, 0.0039 mol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.00013 mol) followed by S-Phos (0.054 g, 0.00013 mol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 110° 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 15% ethyl acetate in hexane as eluent to afford the title compound as a brown semi solid (0.4 g, 57.3%). Mass spectrum (m/z): 525.2 (M+1).

Provenance & Evidence