Dimethylformamide → Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

HRID 507365

Reaktionsgleichung

Reaktionsgleichung von HRID 507365
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1COCC1>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:16]#[N:17])[CH:3]=2)[NH:7][CH:6]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 3602525-Bromo-N,N-Dimethyltryptamine

Produkt 1

HCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-Ausbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Under an inert atmosphere a flask is charged with [2-(5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine (Example 3) (1.0 g, 3.74 mmol), zinc cyanide (0.235 g, 2 mmol), Pd2(dba)3xCHCl3 (0.194 mg, 5 mol %), dppf (bis-diphenylphosphino ferrocene) (0.207 g, 0.374 mmol, 10 mol %), and DMF (12 mL). The orange slurry is heated to 110° C. and stirred for 21 hours. To the black suspension, which has formed, THF (100 mL) is added, and this is extracted with 1 N NaOH (100 mL). The organic layer is washed with water twice (50 mL each), dried and removal of the solvent gives the title product (0.67 g, 84%) as brown solid.

Aufarbeitung

  1. customTo the black suspension, which has formed
  2. extractionthis is extracted with 1 N NaOH (100 mL)
  3. washThe organic layer is washed with water twice (50 mL each)
  4. customdried
  5. customremoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-09bc7caaf0df4d24a634d17d0e98d023
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786156B2

Verknüpfte Notizen

Wird geladen…