Ethylenediamine → HCID 59161290, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve a 65:35 mixture of N-[6-bromo-7-fluoro-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide and N-[6-bromo-5-fluoro-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (500 mg, 1.08 mmol; Preparation 20) in N-methylpyrrolidinone (10 mL). Sparge the resulting solution with nitrogen for 30 min, then add copper(I) cyanide (291 mg, 3.25 mmol) and copper(I) iodide (619 mg, 3.25 mmol). Heat to 130° C. for three days, then cool to room temperature. Dilute the reaction mixture with EtOAc (200 mL) and water (100 mL). Add ethylene diamine until all the solids are dissolved (about 20 mL). Separate the layers, then wash the organic layer with water (3×75 mL). Dry the organic portion (MgSO4), filter, and concentrate the organic layer to afford 474 mg of crude product. Separate the title compound from this mixture by silica gel chromatography (0-10% EtOAc/CHCl3), affording the title compound as a white solid in 20% yield. MS (ES): m/z 408 (M+1), 406 (M−1); HPLC: Rt=2.51 min, (96%).

Provenance & Evidence