Ethylenediamine → 5-cyclopropyl-1H-indazole

Participants

Reaction Steps

In a 1 L round-bottomed flask, 5-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (1.7 g, 5.89 mmol) was dissolved in a solution of dichloromethane (292 mL) and trifluoroacetic acid (194 mL). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure. The resultant crude solid was dissolved in dichloromethane and ethylenediamine (24.2 mL, 5.89 mmol) was added. After stirring at room temperature overnight, the reaction mixture was poured onto water (50 mL) and extracted with EtOAc (2×100 mL). The organic layers were dried over MgSO4 and concentrated under reduced pressure to afford 1 g of 5-cyclopropyl-1H-indazole that was used without further purification.

Provenance & Evidence