Potassium Carbonate → 2-(4-(Quinolin-7-yl)phenyl)acetonitrile

HRID 1525868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525868
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[CH:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N:26]1[C:27]2[C:22](=[CH:21][CH:20]=[C:19]([C:2]3[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=3)[CH:28]=2)[CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 592961167-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Quinoline

Produkt 1

HCID 712709262-(4-(Quinolin-7-yl)phenyl)acetonitrileAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-(4-bromophenyl)acetonitrile (2.55 mmol) in 1,4-dioxane (5 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (2.64 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.083 mmol), and 2M aq potassium carbonate (5.10 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture irradiated in a Biotage Initiator Microwave at 120° C. for 20 min. The resulting black mixture was diluted with water (100 mL) and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-100% ethyl acetate/hexanes) afforded the title compound as a yellow solid (424 mg, 64%). MS(ES)+ m/e 245.3 [M+H]+.

Aufarbeitung

  1. customThe reaction vessel was purged with nitrogen
  2. customsealed
  3. customthe mixture irradiated in a Biotage Initiator Microwave at 120° C. for 20 min
  4. additionThe resulting black mixture was diluted with water (100 mL)
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by silica gel chromatography (0-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-85c2084202434537b52b323faa031d87
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09084794B2

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