6-Methoxyquinoline-2-carbonitrile → HCID 178487953, Verbindung

HRID 1490910

Reaktionsgleichung

Reaktionsgleichung von HRID 1490910
COc1ccc2nc(C#N)ccc2c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>COc1ccc2nc(C#N)cc(B3OC(C)(C)C(C)(C)O3)c2c1

Komponenten

6

Edukt 1

HCID 2304816-Methoxyquinoline-2-carbonitrile

Produkt 1

HCID 178487953HCID 178487953, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

General procedure B was applied to 6-methoxyquinoline-2-carbonitrile (184 mg, 1.00mmol). The reaction was stirred at room temperature for 48 hours. Upon completion,volatiles were removed under reduced pressure and the remaining residue was purified by silica gel flash-column chromatography with gradient elution of MeOH/DCM from 0.5 -12.5% over 25 column volumes, affording 6-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline-2-carbonitrile as a off-white solid (270 mg, 87%);

Quellen und Nachweise

ORD-Eintrag
ord-5c863801736b4499b0d1a54e4561f8db
Quelldatensatz
Borylation dataset from Roche

Verknüpfte Notizen

Wird geladen…