Sodium 3-formylindol-1-ide synthesis

Yield:890095-85-9 86%

Reaction Conditions:

with copper(I) oxide;potassium carbonate in N,N-dimethyl-formamide; for 72 h;Reflux;

Steps:

General procedure for preparation of compounds 2a-2n

General procedure: A suspension of indole-3-carbaldehyde 1 (0.411 g, 2.8 mmol),Cu2O (0.3 equiv), K2CO3 (2.0 equiv) and aryl halide (2.0 equiv) inanhydrous DMF (5.6 mL) was refluxed for 72 h. After cooling to RT,the reaction mixture was filtrated over a celite pad eluting withEtOAc. Solvents were removed and the residue dissolved in EtOAc(20 mL) washed successively by 2.5% aqueous NH4OH, 1 M HCl andsaturated aqueous NaCl. The organic phase was dried over Na2SO4,filtered and concentrated. The residue was purified by flash columnchromatography on silica gel (PE/EtOAc 9:1 to 7:3) to furnish thedesired compound.

References:

Sagnes, Charlène;Fournet, Guy;Satala, Grzegorz;Bojarski, Andrzej J.;Joseph, Beno?t [European Journal of Medicinal Chemistry,2014,vol. 75,p. 159 - 168]