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ChemicalBook CAS DataBase List 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole
894807-98-8

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-pyrazole synthesis

3synthesis methods
269410-08-4 Synthesis
4-Pyrazoleboronic acid pinacol ester

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

76513-69-4 Synthesis
2-(Trimethylsilyl)ethoxymethyl chloride

76513-69-4
362 suppliers
$6.00/1g

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Yield: 86%

Reaction Conditions:

with potassium carbonate in 1-methyl-pyrrolidin-2-one at 20; for 16 h;Inert atmosphere;

Steps:

15.A
Synthesis of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2~yl)-1-((2- (trimethylsilyl)ethoxy)methyl)-1 t-15a)lnt-15aTo a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)- H- pyrazole (8.2 g, 41 mmol) in NMP (60 mL) was added K2C03 (12 g, 82 mmoi) and 2-(trimethylsilyi)ethoxymethy. chloride (7.8 mL, 43 mmol) in sequence. The reaction mixture was stirred at r.t. under N2 for 16 h. Then, the reaction mixture was diluted and filtered, and then the filtrate was diluted with EtOAc (300 mL). The resulting solution was washed with sat. NaHC03 (aq) (3 x 200 mL), H20 (4 x 200 mL), brine (1 x 200 mL), dried over Na2S04, filtered, concentrated and dried in vacuo to yield intermediate .nt-15a (11.4 g, 86 %) as a clear yellowish oil.

References:

SCHERING CORPORATION;TSUI, Hon-Chung;PALIWAL, Sunil;KIM, Hyunjin, M.;KEREKES, Angela, D.;CAPLEN, Mary Ann;ESPOSITE, Sara, J.;MCKITTRICK, Brian, A.;FISCHMANN, Thierry Olivier;DOLL, Ronald, J.;RAINKA, Matthew Paul;LI, Ang WO2011/149874, 2011, A2 Location in patent:Page/Page column 81-82