Nitrogen → 3-(4-chloropyrimidin-2-yl)-5-(2,6-difluorophenyl)-1-tosyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-indole (2.0 g, 3.92 mmol) and 4-chloro-2-tributylstannanyl-pyrimidine (2.38 g, 5.98 mmol) in DMF (60 mL) was bubbled N2 for 15 min and added CuI (0.898 g, 4.71 mmol) and Pd(PPh3)4 (0.226 g, 0.196 mmol). The reaction mixture was heated at 80° C. for 1 h and cooled to RT. The reaction mixture was quenched with water and precipitate was formed. The resulting precipitate was collected by filtration, washed with water, and dried to yield crude product. Purification by silica gel column chromatography, eluting with 10% EtOAc in hexanes obtained the title compound (0.50 g, 26%). MS (ESI, pos. ion) m/z: 496.0 (M+1).

Provenance & Evidence