Dimethylformamide → HCID 58495553, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere add 6-chloro-3-[N-(cyclohexyl)-N-(2,2,2-trifluoroacetyl)-aminomethyl]-pyridine (3.7 g, 11.5 mmol), zinc cyanide (2.02 g, 17.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.48 g, 0.57 mmol) and DPPF (0.63 g, 1.15 mmol) to DMF (40 mL). Heat the mixture at 95° C. for 2 h. Cool the mixture to room temperature and dilute with water and EtOAc. Separate the layers and extract the aqueous layer with EtOAc. Wash the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (400 g) eluting with hexane/EtOAc (1:0 to 3:2 gradient) to obtain the desired intermediate (3.33 g, 93%). MS (APCI+) m/z: 312 (M+H)+.

Provenance & Evidence