Water → HCID 22396680, compound

Participants

Reaction Steps

A mixture of 3-benzyl-10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.71 g, 2.00 mmol), benzophenone imine (0.44 g, 0.40 mL, 2.40 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.037 g, 0.040 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.075 g, 0.120 mmol), and sodium tert-butoxide (0.269 g, 2.80 mmol) in toluene (20.0 mL) was refluxed for 16 h. After cooling to room temperature, water and ethyl acetate were added, and the pahases separated. The aqueous layer was extracted with ethyl acetate (2×). The combined ethyl acetate solution was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography (silica gel, 30% EtOAc/hexane, 1% Et3N) to afford a yellow fluffy solid as the title compound (0.855 g, 94%): mp>71° C. (dec.); 1H NMR (300 MHz, CDCl3) δ 7.82-7.80, 7.65, 7.66-7.11, 6.82-6.79, 6.73, 5.95, 3.78, 3.20-3.16, 2.90-2.78; MS (ESI+) m/z 456 (M++H).

Provenance & Evidence