Sodium Iodide → HCID 15293733, compound

Participants

Reaction Steps

The 4-hydroxyindole-2-carboxamide (EXAMPLE 5, 0.44 g), 4-(1-piperazinyl)-2,6-di-1-pyrrolidinylpyrimidine (0.525 g, 1.74 mmol), powdered potassium carbonate (0.12 g, 0.87 mmol) and sodium iodide (0.075 g) are combined in acetonitrile (50 ml) and heated at reflux for 96 hr. Although TLC showed starting material remained in the reaction mixture, the mixture is concentrated under reduced pressure and the residue partitioned between 1N potassium bicarbonate and methylene chloride. The layers are separated, the aqueous layer is extracted with methylene chloride. The pooled organic extract is washed with water, then saline, dried over magnesium sulfate and concentrated. The residue is chromatographed over silica gel (250 ml) and eluted with methanol/methylene chloride (3.5/96.5). The appropriate fractions are pooled and concentrated; crystallization from acetonitrile gives 4-[3-[4-[2,4-dipyrrolidino-6pyrimidinyl]-1-piperazinyl]propoxy]indole-2-carboxamide, mp 151°-2° (foam). The proposed structure is supported by NMR, IR and mass spectra.

Provenance & Evidence