Dimethylformamide → HCID 18009111, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the crude product from Step G (39.1 mmol) and Zn(CN)2 (4.59 g, 39.1 mmol) in 50 mL of DMF was degassed by bubbling argon through the mixture for 30 minutes. Tetrakis(triphenylphosphine)palladium (3.15 g, 2.73 mmol) was added, and the reaction was heated to 80° C. The solution was stirred over the course of 7 days, twice adding additional portions (2.0 mmol) of palladium catalyst. After cooling to room temperature, the solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (10-15% EtOAc/hexane) provided the titled compound along with some of the aryl bromide starting material.

Provenance & Evidence