Cesium carbonate → Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1H-indazole-5-carbonitrile (D1) (3.88 g, 27.3 mmol) in DMF (85 ml) was added Cs2CO3 (17.8 g, 54.6 mmol) and then ethyl 3-bromopropanoate (3.5 ml), 27 mmol) and ethyl 3-chloropropanoate (3.3 g, 24.2 mmol) were added. The reaction mixture was stirred at 80° C. for 4 hours and then allowed to cool. The solvent was removed in vacuo and the crude material was partitioned between EtOAc and water, the organics were separated, washed with brine, dried and evaporated. The crude was azeotroped with toluene and then purified by flash chromatography (EtOAc/hexane 1:9 to 1:1) to give 3.84 g of a yellow gum. MS data as for previous example.

Provenance & Evidence