Triphenylphosphine → HCID 86622785, compound

Participants

Reaction Steps

Dissolve 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 g, 2.35 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.03 equiv.), copper(I) iodide (0.06 equiv.) and triphenylphosphine (0.25 equiv.) in triethylamine/DMF (3:1, 4 mL). Stir the mixture for 5 min at ambient temperature, add N-prop-2-ynyl-cyclopentylcarboxamide (430 mg, 2.82 mmol) and heat at 70° C. for 18 h in a sealed tube. Cool the reaction mixture to ambient temperature, dilute with EtOAc/hexane (1:1) and wash with water. Dry the organic fraction over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1 to 7:3) to obtain 7-chloro-6-[3-(cyclopentanecarbonyl-amino)-prop-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (500 g, 50%).

Provenance & Evidence