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ChemicalBook CAS DataBase List Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate
1220968-24-0

Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanoate synthesis

2synthesis methods
269410-08-4 Synthesis
4-Pyrazoleboronic acid pinacol ester

269410-08-4
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ethyl (±)-2-bromopropionate

41978-69-2
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Yield:1220968-24-0 61%

Reaction Conditions:

with caesium carbonate in acetonitrile at 90; for 4 h;

Steps:

54.1

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.40 g, 2.1 mmol, Aldrich, Cat. 525057), ethyl 2-bromopropanoate (290 μL, 2.3 mmol), and cesium carbonate (1.5 g, 4.6 mmol) in acetonitrile (8 mL) was stirred at 90° C. for 4 h. After cooling, the reaction mixture was worked up with aqueous Na2CO3, extracted with ethyl acetate (3×20 mL), and washed with brine. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.42 g, 61%). LCMS (M+H)+: m/z=295.1.

References:

US2012/165305,2012,A1 Location in patent:Page/Page column 43