Nitrogen → HCID 86690326, compound

Participants

Reaction Conditions

Reaction Steps

A mixture comprising 7-(2-bromo-3-chloro-6-cyclopropyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate D)(400 mg, 0.933 mmol) in 1,4-dioxane (8 ml) degassed with N2 was treated with phenylboronic acid (120 mg, 0.980 mmol), potassium carbonate (284 mg, 2.052 mmol) and PdCl2(dppf)-CH2Cl2-adduct (76 mg, 0.093 mmol). The reaction mixture was stirred at 60° C. for 12 hours. After cooling to RT and degassing with N2, phenylboronic acid (171 mg, 1.399 mmol) and PdCl2(dppf)-CH2Cl2-adduct (76 mg, 0.093 mmol) were added and stirring continued at 110° C. for 24 hours. The mixture was treated with ice-cooled water and the aqueous was extracted with diethyl ether. The organic portion was dried (Na2SO4) and concentrated under reduced pressure. Purification of the crude product on silica eluting with 5% EtOAc in iso-hexane afforded the titled compound:

Provenance & Evidence