Tris(1,1-dimethylethyl)phosphine → [4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)-2-methylphenyl]cyanamide

Participants

Reaction Steps

(4-bromo-2-methylphenyl)cyanamide (0.698 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium (76 mg, 0.083 mmol), N-methyl-5-cyanopyrroleboronic acid (1.1 g, 7.3 mmol), and potassium fluoride (0.776 g, 13.2 mmol) were placed in a 40 mL vial fitted with a septa. The vial was then filled with a continuous flow of nitrogen and THF (10 mL) was added with stirring. Then tri-tert-butylphoshine (10 wt % in hexane) (0.486 mL, 0.083 mmol) was added to the mixture and allowed to stir 3 hours. The mixture was then diluted with 1/1 hexane/ethylacetate and filtered through a plug of silica gel, the reaction was concentrated and the residue was flash chromatographed using 4/1 Hexane/THF to give (0.062 g, 7%) of the title compound.

Provenance & Evidence