7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 59787411, compound

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Reaction Steps

In an oven dried flask degas DMF (20 mL) by gently bubbling nitrogen gas for 2 h. Add then 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.0 g, 2.35 mmoles), N-pent-4-ynyl-cyclopentylcarboxamide (842 mg, 4.7 mmoles), copper iodide (134 mg, 0.705 mmoles), triethylamine (4.7 mL), tetra-n-butylammonium iodide (2.6 g, 7.05 mmoles) and bis(triphenylphosphine)palladium(II) chloride (165 mg, 0.235 mmoles) and heat the resulting mixture at 80° C. under nitrogen atmosphere while stirring overnight. Concentrate the mixture in vacuo, and then filter through a short pad of Celite® eluting with EtOAc. Purify the residue by chromatography on silica gel eluting with dichloromethane/EtOAc/cyclohexane (3:5:1) to obtain the desired intermediate as an oil (726 mg, 68%). MS (ES+) m/z=455.1 (M+H)+.

Provenance & Evidence