Sodium hydride → 3-[1-(6-Chloromethyl-pyridin-2-ylmethyl)-indol-3-yl]-4-(1-methyl-indol-3yl)-furan-2,5-dione

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil, 42 mg, 1.8 mmol), 3-(1-methyl-indol-3-yl)-4-(indol-3yl)-furan-2,5-dione (236 mg, 0.7 mmol) and dimethylformamide (8 mL) were stirred at room temperature for 1 h. The reaction mixture was cooled with ice and 2,6-bis-chloromethyl-pyridine (520 mg, 3.0 mmol) was added in one portion. Stirring was continued at room temperature for 65 h. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried with MgSO4, filtered and evaporated. Chromatography (ethyl acetate/heptane:50/50) gave the title compound, which was not pure. Further purification by Kugelrohr distillation (oil pump, 150° C.) afforded 156 mg of the sub-title product.

Provenance & Evidence