7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 2,3,4,5-Tetrahydro-1H-benzo(d)azepine

Participants

Reaction Steps

Use a method similar to the General Procedure 1-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (586 mg, 1.37 mmol) with 3-aminomethyl-6-[(2,2-dimethylpropyl)thiomethyl]-pyridine (340 mg, 1.51 mmol) in 1,4-dioxane (15 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1 and 3:1) followed by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1). Concentrate in vacuo to obtain 7-chloro-6-{6-[(2,2-dimethyl-propylthiomethyl)-pyridin-3-ylmethyl]-amino}trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (0.2 g, 29%).

Provenance & Evidence