Ammonia → 5-(2-Methoxy-ethoxy)-3-methyl-pyridine-2-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-3-methyl-pyridine-2-carboxylic acid ethyl ester (3.3 g, 13.52 mmol) and CuI (0.515 g, 2.70 mmol) were dissolved in 2-methoxy-ethanol (10.29 g, 135 mmol) and DMF (2.5 ml). NaH (60%, 0.541 g, 13.52 mmol) was carefully added and the reaction mixture was warmed to 110° C. for 8 h. The reaction mixture was allowed to cool to rt and NH3 in EtOH (10%, 30 ml) was added. The reaction mixture was placed in an autoclave and heated to 100° C. for 20 h. The reaction mixture was cooled to rt, concentrated and purified by column chromatography (silica gel; DCM/0-4% i-Propanol) to give the desired product (1 g, 4.52 mmol).

Provenance & Evidence