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

HRID 1490499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490499
CN1CCc2ccccc21>B1Oc2ccccc2O1.C1=CC2C=CC1C2.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CN1CCc2cc(B3OC(C)(C)C(C)(C)O3)ccc21

Komponenten

8

Edukt 1

HCID 558301-Methyl-2,3-dihydro-1H-indole

Produkt 1

HCID 242295911-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indoleAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 6425PinacolReagenzHCID 8471TriethylamineReagenzHCID 8473NorbornadieneReagenzHCID 67506CatecholboraneReagenzHCID 582056Tris(pentafluorophenyl)boraneKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Prepared from 1-methylindoline (1j, 13.5 mg, 0.100 mmol, 1.00 equiv), catBH (24.0 mg, 0.200 mmol, 2.00 equiv), norbornadiene (9.2 mg, 0.10 mmol, 1.00 equiv) and B(C6F5)3 (5.1 mg, 0.010 mmol, 0.10 equiv) according to GP 3. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3j (7.5 mg, 30%) as a white solid.

Quellen und Nachweise

ORD-Eintrag
ord-a69ae003920743bcb48cb3ac16966ce5
Quelldatensatz
Borylation dataset from Roche

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