Water → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 2360602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2360602
[Cu][C:2]#[N:3].Br[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][N:6]=1.O>CN(C=O)C>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:2]#[N:3])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrileAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Copper(I) cyanide (21 g, 0.24 mol) was added to a solution of 2,5-dibromo-3-methylpyridine (49, 60 g, 0.24 mol) in dry DMF (200 mL), and the mixture was heated at reflux for 2 h. After cooling to room temperature, water (1500 mL) was added to the mixture and the products were extracted with ethyl acetate (3×300 mL). The combined extracts were washed with water (3×300 mL), brine (300 mL), dried with sodium sulfate and evaporated to dryness. The brown oily residue was subjected to flash column chromatography (silica gel), eluting with chloroform, to yield 50 as a white solid (35 g, 74%): mp 86-88° C. 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J=1.8 Hz, 1H), 7.84 (d, J=1.5 Hz, 1H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 149.75, 140.68, 139.95, 132.25, 124.61, 115.90, 18.59; EIMS m/z 196/198 (M+); CIMS 197/199 (MH+). The 1H NMR spectrum is consistent with previously published data (Bioorg. Med. Chem. 1999, 7, 1845-1855).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionthe products were extracted with ethyl acetate (3×300 mL)
  4. washThe combined extracts were washed with water (3×300 mL), brine (300 mL)
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness
  7. washeluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2aabac76d793456889a3d1ba827bacad
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08686146B2

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