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 6h. 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