Cesium carbonate → HCID 58166520, compound

Participants

Reaction Steps

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol (B-4), 1.0 equiv. in dimethylformamide (0.10 M) at 22° C. was added cesium carbonate (1.5 equiv.) and the resulting mixture was allowed to stir for 30 minutes. At this point, 1-(bromomethyl)-3-iodobenzene (1.5 equiv.) was added to this mixture. The reaction mixture was allowed to stir at 55° C. for 18 hours, after which it was diluted with ethyl acetate and water. The biphasic layers were separated and the organic layer was washed twice with water. The organic layer was dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexanes gradient to provide 2-(4-(3-iodobenzyloxy)-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (4-1) as a solid.

Provenance & Evidence