5-Bromo-3-methyl-2-pyridin-3-yl-1H-indole → 3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

HRID 1630763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1630763
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)=[C:5]2[CH3:17].[Cu][C:19]#[N:20]>>[CH3:17][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:19]#[N:20])[CH:3]=2)[NH:7][C:6]=1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Komponenten

3

Edukt 2

HCID 212605715-Bromo-3-methyl-2-pyridin-3-yl-1H-indoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 445541323-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

5-Bromo-3-methyl-2-pyridin-3-yl-1H-indole (5.0 g, 16.7 mmol) and copper (I) cyanide (1.9 g, 20.1 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 200° C. under N2 with vigorous stirring overnight. The mixture is cooled to room temperature and dichloromethane (200 mL) is added. The mixture is filtered through a pad of celite. The filtrate is washed with 10% aqueous ammonia in saturated aqueous ammonium chloride. The aqueous phase is extracted with dichloromethane. 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 3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.45 (s, 3H), 7.45-7.60 (m, 3H), 8.06-8.11 (m, 1H), 8.15 (s, 1H), 8.60 (dd, J=4.8, 1.5 Hz, 1H), 8.91 (d, J=1.5 Hz, 1H), 11.94 (br. s., 1H). HRMS (ESI) m/z 234.1031 [(M+H)+ Calcd for C15H11N3, 234.1031].

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. additiondichloromethane (200 mL) is added
  5. filtrationThe mixture is filtered through a pad of celite
  6. washThe filtrate is washed with 10% aqueous ammonia in saturated aqueous ammonium chloride
  7. extractionThe aqueous phase is extracted with dichloromethane
  8. dry with materialThe combined organic phase is dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:0)

Quellen und Nachweise

ORD-Eintrag
ord-f033e7c750a64265a0299959d39cd750
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791141B2

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