1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Struktur

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Bezeichnung:1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

CAS-Nr837392-62-8

Englisch Name:1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

CBNumberCB4296474

SummenformelC15H20BNO2

Molgewicht257.14

MOL-Datei837392-62-8.mol

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole physikalisch-chemischer Eigenschaften

Schmelzpunkt	110-114 °C (lit.)
Siedepunkt	391.3±15.0 °C(Predicted)
Dichte	1.05±0.1 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Aggregatzustand	solid
Aussehen	Off-white to light yellow Solid
InChI	InChI=1S/C15H20BNO2/c1-14(2)15(3,4)19-16(18-14)12-6-7-13-11(10-12)8-9-17(13)5/h6-10H,1-5H3
InChIKey	JQLYKUPEQYNDFF-UHFFFAOYSA-N
SMILES	N1(C)C2=C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)C=C1

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	22-24/25
WGK Germany	3
Hazard Note	Irritant
HS Code	2933299090

Gefahreninformationscode (GHS)

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
off-white powder
Synthese

10075-52-2

73183-34-3

837392-62-8

The general procedure for the synthesis of 1-methylindole-5-boronic acid pinacol ester from 5-bromo-1-methyl-1H-indole and biboronic acid pinacol ester is as follows: the synthesis was carried out according to the literature method with appropriate adjustments. To an 8-dram vial equipped with a magnetic stirrer were sequentially added pinacol bis(boronic acid) ester (2 mmol, 508 mg), 5-bromo-1-methyl-1H-indole (2.1 mmol, 441 mg), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.06 mmol, 44 mg), potassium acetate (6 mmol, 589 mg), and degassed 1,1'-bis(diphenylphosphino)ferrocene(III). ), and degassed 1,4-dioxane (10 mL). The reaction mixture was purged under a strong stream of nitrogen for 5 min to deoxygenate, followed by transferring the reaction system to an oil bath preheated to 80 °C with continuous stirring for 48 h. The reaction was carried out in a cooled room with a temperature range of 0.5 °F to 0.5 °F. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered through a diatomaceous earth pad and washed with ethyl acetate (50 mL). The filtrates were combined and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography with petroleum ether as eluent, followed by a 5% to 12% gradient elution of ether/petroleum ether to afford 342 mg (67% yield) of the target product, 1-methylindole-5-boronic acid pinacol ester, as a white solid.
Einzelnachweise
[1] Synlett, 2018, vol. 29, # 15, p. 2031 - 2034
[2] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003
[4] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[5] Patent: WO2016/180537, 2016, A1. Location in patent: Page/Page column 133

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Upstream-Materialien And Downstream Produkte

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