Triethylamine → 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carbonitrile

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)-piperidine-1-carboxylate (0.3 g, 0.63 mmol) in dichloromethane (5 mL) trifluoroacetic acid (2.0 mL) was added at 0° C. and stirred at room temperature for 2-3 h. The solvent was removed in vacuo and the resulting residue was dissolved in dichloromethane (5 mL), triethylamine (0.193 g, 1.91 mmol) and the cyanogen bromide (0.101 g, 0.95 mmol) were added at 0° C. and stirred at room temperature for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give 4-((6-(5-(methylsulfonyl)-1H-indol-1-yl)pyridin-3-yl)oxy)piperidine-1-carbonitrile (0.160 g, 63%); MS: 397 (M+1).

Provenance & Evidence