3-Hydroxypyridine → 2-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-4-(pyridin-3-yloxy)-benzoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-{[(2,4-dimethoxy-phenoxy)-ethoxycarbonylmethyl-amino]-methyl}-benzoic acid ethyl ester (3.292 g), pyridin-3-ol (887 mg), CuCl (330 mg), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 0.26 mL), cesium carbonate (3.26 g) in NMP (6 mL) was heated at 130° C. for 24 h. Then the reaction was cooled, diluted with EtOAc, solids were filtered off, filtrate was washed with water, diluted NaCl solution, dried over sodium sulfate, filtered off, concentrated; the residue was column purified to give the desired product (1.71 g). LC MS ESI+: 509 (M+1)+.

Provenance & Evidence