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

1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole synthesis

6synthesis methods

Product Name:1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
CAS Number:1029716-44-6
Molecular formula:C13H23BN2O3
Molecular Weight:266.14

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1195-66-0 Synthesis

2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1195-66-0
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1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

1029716-44-6
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$6.00/250mg

Yield:1029716-44-6 99%

Reaction Conditions:

Stage #1: 4-bromo-1-(1-ethoxyethyl)-1H-pyrazolewith isopropyl magnesium chloride - lithium chloride complex in tetrahydrofuran at 20 - 25; for 16 h;
Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran at -20 - 25; for 2 h;

Steps:

18.3

Step 3[00251j To an oven-dried vial was charged a solution of isopropyl magnesium /lithium chloride solution (1.0 M in THF) (6.32 ml, 8.22 mmol) at room temperature, andto this solution was added 4-bromo-1-(1-ethoxyethyl)-1H-pyrazole (1.00 g, 4.56 mmol)dropwise and the resulting mixture was stirred at room temperature for 16 h. Theresulting solution was then cooled to -20 °C and 2-methoxy-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (1.73 1 g, 10.95 mmol) was added via syringe and the resulting mixture was allowed to warm to rt. After 2h at room temperature, the reaction was quenched by addition of aq. sat. ammonium chloride (15 mL) causing a white precipitate to form.After diluting with additional water (20 mL), the mixture was extracted with hexanes (140 mL x 2) and the combined extracts were washed with aq. sat. sodium bicarbonate, brine, then dried over sodium sulfate, filtered and concentrated to afford 1.20 g (99%) of the product as a colorless oil

References:

WO2014/74661,2014,A1 Location in patent:Paragraph 00251

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