2-Chloro-4-(tributylstannyl)pyrimidine → 5-(3-(2-chloropyrimidin-4-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (1.00 g, 1.914 mmol) and 2-chloro-4-(tributylstannyl)pyrimidine (0.966 g, 2.393 mmol) in DMF (5 mL) followed by tetrakis(triphenylphosphine)palladium (0.111 g, 0.096 mmol) and CuI (0.016 mL, 0.479 mmol). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 1 h. The mixture was diluted with DCM and washed with water (3×50 mL) and brine. The organic layer was dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 5-40% EtOAc in Hexanes) to give 5-(3-(2-chloropyrimidin-4-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (672 mg, 1.320 mmol, 69.0% yield) as a brown solid. MS (ESI, pos. ion) m/z: 509.0 (M+1).

Provenance & Evidence