2-(tetrahydro-2H-pyran-4-yloxy)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile synthesis
- Product Name:2-(tetrahydro-2H-pyran-4-yloxy)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
- CAS Number:1292317-54-4
- Molecular formula:C18H24BNO4
- Molecular Weight:329.2
876918-62-6
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Yield:1292317-54-4 98%
Reaction Conditions:
with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 in 1,4-dioxane at 80; for 20 h;
Steps:
I-4.2
To a solution of 5-bromo-2-(tetrahydro-2H-pyran-4-yloxy)benzonitrile (2.7 g, 9.6 mmol) in /?-dioxane (50 mL) was added Pd(dppf)Cl2-CH2Cl2 (0.408 g, 0.50 mmol), and KOAc (2.94 g, 30 mmol). After stirring at 80 °C for 20 h, the mixture was filtered to remove KOAc and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Si02, EtOAc/Hexanes, 0-60%>) to afford the title compound (3.1 g, 98%>).
References:
MYREXIS, INC.;HOLCOMB, Ryan;SUZUKI, Kazuyuki;HALTER, Robert J.;SEBAHAR, Paul R.;MCLEOD, Donald A.;SHENDEROVICH, Mark D.;YAGER, Kraig M.;BURSAVICH, Matthew Gregory;YUNGAI, Ashantai J.;RICHARDS, Burt;BARTEL, Paul L.;WETTSTEIN, Daniel A. WO2011/46970, 2011, A1 Location in patent:Page/Page column 95
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