Methyl iodide → isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)(methyl)amino)phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

Methyl iodide (17 mg, 0.122 mmol) and sodium hydride (60% dispersion of mineral oil, 1.1 mg, 0.045 mmol) were added to a solution of isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate (17 mg, 0.041 mmol) and dimethylformamide (2 mL) in a 50 mL round bottom flask at room temperature. The mixture was then heated to 50° C. and allowed to stir overnight. The solution was quenched with saturated ammonium chloride (25 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (1×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by preparative TLC (1000 mm thickness, 30% ethyl acetate/hexanes) to afford 12 mg (68%) of isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)(methyl)amino)phenoxy)acetate.

Provenance & Evidence