2-Methylindole → 2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

HRID 1490566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490566
Cc1cc2ccccc2[nH]1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>Cc1cc2cccc(B3OC(C)(C)C(C)(C)O3)c2[nH]1

Komponenten

6

Edukt 1

HCID 72242-Methylindole

Produkt 1

HCID 249605942-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 138539Cyclopentyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The general procedure A was followed using 2-methyl-1H-indole (65.6 mg, 0.5 mmol.) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 50 oC. 5y was obtained as white solid (82.3 mg, 64 %) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v). m.p.: 73-75 oC.

Quellen und Nachweise

ORD-Eintrag
ord-8a9da9cdfb524f499e336b80310520a5
Quelldatensatz
Borylation dataset from Roche

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