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ChemicalBook CAS DataBase List 1-(2-Methoxyethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

1-(2-Methoxyethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole synthesis

6synthesis methods
269410-08-4 Synthesis
4-Pyrazoleboronic acid pinacol ester

269410-08-4
389 suppliers
$5.00/1g

627-42-9 Synthesis
2-Methoxyethyl chloride

627-42-9
271 suppliers
$6.00/5g

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Yield:847818-71-7 100%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 160; for 0.5 h;Microwave irradiation;

Steps:

B162 Compound B162a. 1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

4-( 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 00 mg, 0.52mmol), 1-chloro-2-methoxyethane (0.056 mL, 0.62 mmol) and cesium carbonate (252mg, 0.73 mmol) in DMF (1 mL) were heated in microwave reactor at 160 °C for 30 min.The reaction mixture was concentrated under reduced pressure and purified by silica gelchromatography (ISCO, hexanes/ethyl acetate 0-100% over 15 min) to isolate CompoundB162a (130 mg, 100% yield). HPLC: RT = 1.0 min (LCMS Method M). MS (ES): m/z= 253.0 [M+H( 1H NMR (500MHz, CHLOROFORM-d) 8 8.04 (s, 1H), 7.83 (d,J=18.4 Hz, 1H), 4.37 (t, J=5.2 Hz, 1H), 3.78 (t, J=5.2 Hz, 1H), 3.38-3.31 (m, 2H), 2.98(s, 3H), 2.90 (s, 3H), 1.34 (s, 6H), 1.26 (s, 3H).

References:

WO2014/15088,2014,A1 Location in patent:Paragraph 00223