Formic Acid → HCID 59161186, compound

Participants

Reaction Conditions

Reaction Steps

Add Al—Ni catalyst [12635-27-7] (3.0 g) to a solution of (R)-N-(6cyano9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 123) (2.50 g, 6.42 mmol) in formic acid (96%, 40 mL) and water (5 mL). Heat the reaction mixture to 90° C. for 18 h, then add 2 g fresh Al—Ni catalyst. Heat to reflux for 18 h, cool to 60° C., dilute with MeOH (30 mL), and resume heating. When reflux has begun, filter the reaction mixture while hot through filter paper. Concentrate the filtrate in-vacuo. Dilute the residue with water (30 mL) and saturated aqueous NaHCO3 (30 mL), then extract into EtOAc (3×150 mL). Dry the organics (MgSO4), filter, and concentrate to give 2.25g (89%) of the title compound as a brown solid. MS (ES): m/z 393 (M+1); HPLC (Method B): Rt=4.57 min (91%).

Provenance & Evidence