4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-(TRIISOPROPYLSILYL)-1H-INDOLE synthesis
- Product Name:4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-(TRIISOPROPYLSILYL)-1H-INDOLE
- CAS Number:690632-17-8
- Molecular formula:C23H38BNO2Si
- Molecular Weight:399.45
13154-24-0
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388116-27-6
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$15.00/250mg
690632-17-8
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$112.00/250mg
Yield:-
Reaction Conditions:
with sodium hydride in tetrahydrofuran at 0 - 5;
Steps:
25-26.b
To a stirred mixture of sodium hydride (60% disp. in oil, 365 mg, 9.1 mmol, 1.06 eq.) in THF (7 mL) at ca. 0° C. was added a THF (8 mL) solution of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (2.1 g, 8.64 mmol, 1 eq., 75% purity) dropwise under N2. The mixture was stirred at 0°-5° C. for 30 min., whereupon triisopropylsilyl chloride (2.03 mL, 9.5 mmol, 1.1 eq.) was added dropwise. The reaction mixture was stirred under N2 returning to ambient overnight. The reaction was quenched with the addition of water and the organics were extracted into EtOAc. The organic phase was washed with H2O, brine, dried over MgSO4, filtered and concentrated to an oil, which was chromatographed (2% EtOAc/hexanes) yielding 1.59 g of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole, as a white solid.
References:
US2006/270686,2006,A1 Location in patent:Page/Page column 31
52488-36-5
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$15.00/1g
690632-17-8
24 suppliers
$112.00/250mg
73183-34-3
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$6.00/5g
690632-17-8
24 suppliers
$112.00/250mg