Water → (R)-tert-butyl 3-(6-(5-(6-isopropoxy-pyrazin-2-yl)-1-tosyl-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

3-Iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole (0.4 g, 0.753 mmol) and (R)-tert-butyl 3-(6-(tributylstannyl)pyrazin-2-ylamino)piperidine-1-carboxylate (0.51 g, 0.903 mmol) in DMF (10 mL) was purged with argon for 15 min and added CuI (225 mg, 1.18 mmol) and Pd(PPh3)4 (105 mg, 0.09 mmol). The reaction mixture was heated at 100° C. for 2 h and cooled to RT. To the reaction mixture was added water and precipitate was formed. The precipitate was collected by filtration, washed with water and dried overnight. The crude product was purified by chromatography (eluting with 50% EtOAc/hexane) to obtain (R)-tert-butyl 3-(6-(5-(6-isopropoxy-pyrazin-2-yl)-1-tosyl-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate (0.2 g, 57%). MS (ESI, pos. ion) m/z: 684 (M+1).

Provenance & Evidence