5-bromo-2-pyridin-3-yl-1H-indole → 2-pyridin-3-yl-1H-indole-5-carbonitrile

HRID 593495

Reaktionsgleichung

Reaktionsgleichung von HRID 593495
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[CH:5]2.[Cu][C:18]#[N:19]>>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([C:18]#[N:19])=[CH:10][CH:9]=3)[CH:12]=1

Komponenten

3

Edukt 2

HCID 670933625-bromo-2-pyridin-3-yl-1H-indoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 445541352-pyridin-3-yl-1H-indole-5-carbonitrile

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

5-Bromo-2-pyridin-3-yl-1H-indole (7.0 g, 21.8 mmol) and copper (I) cyanide (2.3 g, 26.1 mmol) are placed in a round bottom flask which is flushed with N2. N-Methylpyrrolidinone (40 mL) is added via syringe. The resulting mixture is heated to 160° C. under N2 with vigorous stirring overnight. The mixture is cooled to room temperature and poured into 10% aqueous ammonia in saturated aqueous ammonium chloride (300 mL). The aqueous phase is extracted with dichloromethane (100 mL) five times. The combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:0) to give 2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.20 (s, 1H), 7.48 (dd, J=8.3, 1.5 Hz, 1H), 7.51-7.55 (m, 1H), 7.59 (d, J=8.6 Hz, 1H), 8.12 (s, 1H), 8.25-8.29 (m, 1H), 8.56 (dd, J=4.8, 1.5 Hz, 1H), 9.14 (d, J=1.8 Hz, 1H), 12.27 (s, 1H). HRMS (ESI) m/z 220.0869 [(M+H)+ Calcd for C14H9N3, 220.0875].

Aufarbeitung

  1. customwhich is flushed with N2
  2. additionN-Methylpyrrolidinone (40 mL) is added via syringe
  3. temperatureThe mixture is cooled to room temperature
  4. additionpoured into 10% aqueous ammonia in saturated aqueous ammonium chloride (300 mL)
  5. extractionThe aqueous phase is extracted with dichloromethane (100 mL) five times
  6. dry with materialThe combined organic phase is dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:0)

Quellen und Nachweise

ORD-Eintrag
ord-9ba2700b8d8c494cbf999114bb3d9f06
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

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