Lithium aluminum hydride → HCID 58565373, compound

Participants

Reaction Steps

A solution of ethyl 6-chloro-1-(3-fluorophenyl)-1H-indole-2-carboxylate (0.60 g, 1.9 mmol) in tetrahydrofuran (10 mL) was cooled at −78° C. Lithium tetrahydroaluminate (1 M) in tetrahydrofuran (6.0 mL, 6.0 mmol) was added dropwise and the resulting mixture was stirred at this temperature for 1 hour. The reaction was quenched by the addition of water (0.12 mL) and stirred for 10 minutes, warmed up to room temperature, followed by the addition of 5% aqueous NaOH solution (0.12 mL) with stirring for 10 minutes. Then additional water (0.36 mL) was added and stirring was continued for 10 minutes. The mixture was filtered, dried over MgSO4 and concentrated to give the crude product (0.53 g). The residue was used in the next step directly. LCMS calculated for C15H12ClFNO(M+H)+: m/z=276.1. Found: 276.0.

Provenance & Evidence