Sodium hydride → HCID 86632299, Verbindung

HRID 1929530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929530
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10])#[N:2].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][C:19]=1[CH:20]([CH3:22])[CH3:21].[H-].[Na+]>C1COCC1>[Cl:13][C:14]1[N:15]=[N:16][C:17]([CH:3]([C:1]#[N:2])[C:4]2[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=2)[C:9]#[N:10])=[CH:18][C:19]=1[CH:20]([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27739363-Cyano-4-fluorobenzylcyanideHCID 140241623,6-Dichloro-4-isopropylpyridazine

Produkt 1

HCID 86632299HCID 86632299, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cold solution of 5-(cyanomethyl)-2-fluorobenzonitrile (1 eq) and 3,6-dichloro-4-isopropylpyridazine (1.3 eq) (Reference: Org. Prep.+Proc. Int. 1988, 20, 117 and U.S. Pat. No. 4,628,088, 1986) in THF (38 mL, 0.1 M) was added portionwise NaH (1 eq). The reaction was stirred at 0° C. for 15 min and then warmed to RT and stirred for 2 hrs. The reaction was quenched with a sat. aq. NaHCO3 and extracted with EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by silica gel chromatography, eluting with petroleum ether:EtOAc (8:2) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ: 7.80-7.79 (2H, m), 7.49 (1H, s), 7.31-7.29 (1H, m), 5.63 (1H, s), 3.34-3.28 (1H, m), 1.36-1.29 (6H, m). MS (ES) C16H12ClFN4 required: 314/316. found: 315/317 (M+H)+.

Aufarbeitung

  1. temperaturewarmed to RT
  2. stirringstirred for 2 hrs
  3. customThe reaction was quenched with a sat. aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified by silica gel chromatography
  9. washeluting with petroleum ether:EtOAc (8:2)

Quellen und Nachweise

ORD-Eintrag
ord-4676f021764847a682c5cf1f61d86b89
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188084B2

Notizen zur Reaktion

Wird geladen…