Cesium carbonate → Methyl 3-[[6-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-2,4-dimethyl-benzoate (0.5 g, 0.0015 mol, see preparation 40), tert-butyl-dimethyl-(3-piperidylmethoxy)silane (0.41 g, 0.0018 mol, see preparation 14) and Cs2CO3 (1.95 g, 0.006 mol) in 1,4-dioxane (20 ml) is added Pd2(dba)3 (0.137 g, 0.00015 mol) followed by S-Phos (0.06 g, 0.00015 mol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 80° C. After 24 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 (0.2 g, 38%). Mass spectrum (m/z): 525.2 (M+1).

Provenance & Evidence