3-Fluorobenzyl bromide → N-[5-Chloro-6-cyano-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide

Participants

Reaction Steps

Prepare the title compound by essentially following the procedure as described in Example 96 with N-(7-chloro-6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide and N-(5-chloro-6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide (50:50 mixture—Preparation 17) and 3-fluorobenzyl bromide, to obtain a mixture of regioisomers. Separate the title compound from this mixture of regioisomers using silica gel chromatography (0-20% EtOAc/CHCl3), to afford the title compound in 5% yield. MS (ES): m/z 424 (M+1), 422 (M−1); HPLC (Method B): Rt=6.87 min, (97%).

Provenance & Evidence