Phenylpropanolamine → (1R,2S)-1-[(1-isopropyl-1H-indazol-5-yl)oxy]-1-phenylpropan-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-iodo-1-isopropyl-1H-indazole (30c, 461 mg, 1.26 mmol), (1R,2S)-2-amino-1-phenylpropan-1-ol (286 mg, 1.89 mmol), copper (I) iodide (25 mg, 130 μmol), and cesium carbonate (1.45 g, 3.8 mmol) in butyronitrile (5 ml) was stirred at 125° C. for 2 h. Then the mixture was cooled to room temp., the inorganic material was removed by filtration and washed with ethyl acetate. The combined organic solutions were concentrated i. vac., and the product purified by flash chromatography on silica gel (ethyl acetate/methanol). Yield 200 mg (51%) of a brown oil.

Provenance & Evidence