Fumaric Acid → HCID 131715076, compound

Participants

Reaction Steps

A solution of 6.6 g (19 mmoles) of 1-[(1,1-dimethylethyl)amino]-3-(2-iodophenoxy)-2-propanol, the product of Example 12b., 2.5 g (19.7 mmoles) of p-cyanophenylacetylene, 0.44 g (0.38 mmole) of (Ph3P)4Pd and 0.07 g (0.78 mmole) of copper (I) iodide in 40 ml of deoxygenated triethylamine and 20 ml of deoxygenated THF was stirred under nitrogen for 18 hr. A precipitate was removed by filtration and discarded. The solvent was evaporated from the filtrate in vacuo. Trituration of the residue with ether gave a crystalline solid which was collected by filtration. Evaporation of the ether filtrate gave a second crop of crystalline product. The combined crystalline material was dissolved in MeOH and fumaric acid (0.5 equivalent) was added. There was obtained 5.6 g (75%) of crystalline 4-[2-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenylethynyl]benzonitrile (E)-2-butenedioate hydrate (50:25:17), mp 198°-200° C.

Provenance & Evidence