Cesium carbonate → 6-(4-Methyl-piperazin-1-yl)-1-(toluene-4-sulfonyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

A 250 mL round bottom flask was loaded with 6-Bromo-1-(toluene-4-sulfonyl)-1H-indole (4 g, 11.4 mmol), Cs2CO3 (7.4 g, 22.8 mmol), Pd2dba3 (0.104 g, 0.114 mmol), RuPHOS (0.106 g, 0.23 mmol), Toluene (150 mL), N-Methyl piperazine (1.9 mL, 17.2 mol), evacuated and flushed with nitrogen. Next the reaction flask was heated at 100° C., over the weekend. Analysis at this point showed that most of the starting material had converted to the product. After cooling to room temperature, the solution was diluted with EtOAc (150 mL), filtered through a pad of celite, washed with additional EtOAc (150 mL) and was evaporated. The resulting oil was chromatographed on silica gel to give the product as a thick brown oil (which crystallized on standing), 3.1 g, (73.8% yield).

Provenance & Evidence