Benzyl Bromide → 1-Benzyl-1H-indole-4-carbonitrile

HRID 1777723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777723
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH2:12]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 38176024-Cyanoindole

Produkt 1

HCID 290120411-Benzyl-1H-indole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of indole-4-carbonitrile (2.0 g, 14.1 mmol, 1 eq) and benzyl bromide (2.17 mL, 18.3 mmol, 1.3 eq) in dry DMF (20 mL) was added, at rt, NaH (733 mg, 18.3 mmol, 1.3 eq) portionwise under Ar(g). The resulting reaction mixture was stirred at rt overnight, and was subsequently partitioned with H2O (30 mL), and then extracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-1:3) to furnish the product, 2, as a white solid (3.30 g, 99%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customwas subsequently partitioned with H2O (30 mL)
  3. extractionextracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-1:3)
  7. customto furnish the product, 2

Quellen und Nachweise

ORD-Eintrag
ord-424348a1a8794a57adcde51b968d75db
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266879B2

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