Dimethylformamide → HCID 86692164, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 12 mL of DMF. This was degassed with N2 for 10 min and then added 3-benzyl-1-oxoisoindolin-5-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (609 mg, 1.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (214 mg, 0.23 mmol), 1,1′-bis(diphenylphosphino)ferrocene (142 mg, 0.26 mmol) and zinc (30.6 mg, 0.47 mmol) respectively. This was heated up to 100° C. for 15 min under N2, then added Zinc cyanide (82 mg, 0.70 mmol). This was heated at 100° C. for 2.5 hours, LC/MS showed complete conversion. The reaction mixture was cooled down to room temperature, diluted with ethyl acetate, then filtered through a pad of celite, the filtrate was concentrated down and the residue was purified by flash-chromatography on silica gel with 30-90% ethyl acetate in hexane, 125 mg (43%) of the product was obtained.

Provenance & Evidence