5-(Methylsulfonyl)-1H-indole → tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a mixture of 4-((6-chloropyridin-3-yl)oxy)piperidine-1-carboxylate (intermediate-6) (0.440 g, 1.4 mmol) and 5-(methylsulfonyl)-1H-indole (intermediate-21) (0.261 g, 1.3 mmol) in anhydrous dioxane (5 mL), 2-(2′-Di-tert-butylphosphine) biphenylpalladium(II)acetate (0.130 g, 0.281 mmol) and NaOtBu (sodium tert.butoxide) (0.312 g, 0.960 mmol) were added. The resultant reaction mixture was refluxed for 4-5 h. The reaction mixture was filtered over celite and filtrate was concentrated in vacuo. The residue was purified by flash column chromatography to give tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carboxylate (0.337 g, 50%).

Provenance & Evidence