Isopropyl 2-(3-aminophenoxy)acetate → isopropyl 2-(3-((7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

Approximately forty oven dried 3 Å molecular sieves were added to a solution of 7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one (174 mg, 0.724 mmol) and isopropyl 2-(3-aminophenoxyl)acetate (644 mg, 3.08 mmol) in toluene (15 mL) at 25° C. The reaction was heated in an 120° C. oil bath and allowed to stir overnight for approximately 16 hours. The reaction was cooled to room temperature and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 25 mg (4%) of isopropyl 2-(3-((7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)phenoxy)acetate.

Provenance & Evidence