Diisopropylethylamine → 3-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-nitro-1H-indole

Participants

Reaction Steps

A mixture of 5-nitro-3-(3-bromopropyl)indole (0.57 g, 2.0 mmol), 1-(5-methoxy-4-pyrimidyl)piperazine (0.47 g, 2.4 mmol), KI (0.40 g, 2.4 mmol) and diisopropylethylamine (1.75 mL, 10.0 mmol) in 20 mL of acetonitrile was refluxed under Ar for 6 h. The cooled reaction mixture was diluted with ethyl acetate and washed (H2O, brine). The aqueous wash was back-extracted with CH2Cl2 and the organic phase was washed (H2O, brine). The combined organic phases were dried (Na2SO4) and evaporated, and the residue was chromatographed (SiO2 /CH2Cl2 -MeOH, 95:5) to give a solid. This material was triturated with CH2Cl2 -hexane to give the title compound (0.55 g, 70%) as a yellow solid, m.p. 163°-166° C.

Provenance & Evidence