Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (458 mg, 1.076 mmol) with 4-[(cyclopropanecarbonyl-amino)-methyl]-benzylamine (275 mg, 1.346 mmol) using tris(dibenzylideneacetone)dipalladium(0) (99 mg, 0.108 mmol), BINAP (134 mg, 0.215 mmol) and cesium carbonate (710 mg, 2.17 mmol) in toluene (17 mL). Purify by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 over 5 min, 49:1 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15 over 5 min, 3:1 over 30 min, 1:1; 50 mL/min) to obtain 7-chloro-6-{4-[(cyclopropanecarbonyl-amino)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (335 mg, 65%) as a white solid. MS (ES+) m/z: 480 (M+H)+.
