Palladium-Catalyzed Suzuki-Miyaura Coupling

3-Iodopyrazolopyrimidines or 3-Bromopyrazolopyrimidines (1 equiv.), Na₂CO₃ or K₃PO₄ (2–4 equiv.), Pd(PPh₃)₄ or Pd(II)Cl₂dppf.DCM, (0.05 equiv.) and boronic acids or boronate pinacol esters (1–2 equiv.) were dissolved in a mixture of dimethoxyethane (1.5 mL) and water (0.5 mL) and then heated in a microwave at 80 °C for one hour. The reaction was monitored by thin layer chromatography. After cooling, ethyl acetate and water were added and the organic phase was separated. The water phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over Na₂SO₄ and evaporated under reduced pressure. The crude product was then purified via flash chromatography over silica, eluting with either a hexanes/EtOAc or CH₂Cl₂/MeOH gradient. If necessary, further purification was performed with preparatory RP-HPLC.

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Vidadala R.S., Rivas K.L., Ojo K.K., Hulverson M.A., Zambriski J.A., Bruzual I., Schultz T.L., Huang W., Zhang Z., Scheele S., DeRocher A.E., Choi R., Barrett L.K., Siddaramaiah L.K., Hol W.G., Fan E., Merritt E.A., Parsons M., Freiberg G., Marsh K., Kempf D., Carruthers V.B., Isoherranen N., Doggett J.S., Van Voorhis W.C, & Maly D.J. (2016). Development of an Orally Available and Central Nervous System (CNS)-Penetrant Toxoplasma gondii calcium-dependent protein kinase 1 (TgCDPK1) Inhibitor with Minimal Human Ether-à-go-go-Related Gene (hERG) Activity for the Treatment of Toxoplasmosis. Journal of medicinal chemistry, 59(13), 6531-6546.

Publication 2016

Boronic acids Brine Chromatography Dimethoxyethane Esters Ethyl acetate Hexanes Hplc Microwave Pinacol Pressure Silica Thin layer chromatography

Corresponding Organization :

Other organizations : University of Washington, Washington State University, Portland VA Medical Center, University of Michigan–Ann Arbor, Center for Infectious Disease Research, AbbVie (United States)

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Variable analysis

independent variables

3-Iodopyrazolopyrimidines or 3-Bromopyrazolopyrimidines (1 equiv.)
Na2CO3 or K3PO4 (2–4 equiv.)
Pd(PPh3)4 or Pd(II)Cl2dppf.DCM, (0.05 equiv.)
Boronic acids or boronate pinacol esters (1–2 equiv.)

dependent variables

Reaction progress monitored by thin layer chromatography
Purified product via flash chromatography or preparatory RP-HPLC

control variables

Reaction mixture of dimethoxyethane (1.5 mL) and water (0.5 mL)
Reaction heated in a microwave at 80 °C for one hour

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