Water → HCID 59822322, compound

Participants

Reaction Steps

Combine 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (5.015 g, 11.8 mmol), zinc cyanide (2.09 g, 17.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.59 g, 0.59 mmol) and DPPF (0.659 g, 1.18 mmol) in anhydrous DMF (40 mL), and stir at 95° C. for 3 h. Cool the reaction mixture to room temperature, add DCM and water. Extract the aqueous phase with DCM. Dry the combined organic extracts over anhydrous Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (20:1, 10:1 and 5:1) to obtain the desired intermediate (3.2 g, 90%). MS (ES+) m/z: 303 (M+H)+.

Provenance & Evidence