1,4-Dioxane → HCID 178517858, compound

Participants

Reaction Steps

A mixture of 2-bromo-1-chloro-4-(trifluoromethyl)benzene (26 mg, 0.0001 mol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 0.000002 mol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (5 mg, 0.00001 mol) in 1,4-dioxane (0.5 mL, 0.006 mol) was stirred under N2 (g) for 20 min. To this mixture were added (5S)-2-{trans-4-[(triethylsilyl)oxy]cyclohexyl}-2,7-diazaspiro[4.5]decan-1-one (30 mg, 0.00008 mol) and sodium tert-butoxide (11.8 mg, 0.000123 mol), and the resulting mixture was degassed and stirred at 100° C. for 16 h. At this time 1M TBAF (tetra-n-butylammonium fluoride) in THF (0.3 mL) was added dropwise to the reaction mixture and the solution was stirred at rt for 1 h. The volatiles were removed in-vacuo and the residue was purified by prep-HPLC to afford the desired product. LC-MS: 431.1 (M+H)+.

Provenance & Evidence