Phosphorus oxychloride → Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate

HRID 877660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877660
[C:1]([C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:5]2[C:4]=1O)#[N:2].O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:4]1[C:5]2[N:6]([CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=2)[N:7]=[CH:8][C:3]=1[C:1]#[N:2]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178468548HCID 178468548, Verbindung

Produkt 1

HCID 69326995Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylateAusbeute 48 %

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a round bottom flask was added POCl3 (200 mL) and ethyl 3-cyano-4-hydroxypyrrolo[1,2-b]pyridazine-6-carboxylate (20 g, 80 mmol). The reaction was heated under nitrogen at 75° C. for 2 hours. The reaction was cooled to room temperature and POCl3 was removed under vacuum. The residue was poured onto ice-water. The aqueous solution was extracted with CH2Cl2. The organic layer was washed with saturated sodium carbonate solution, dried and concentrated. The resulting residue was purified by flash silica gel column chromatography to yield 10 g (48%) of the title compound as a yellow solid. H1 NMR (400 MHz, CDCl3) δ ppm: 8.33 (1H, d, J=1.3 Hz), 8.11 (1H, s), 7.41 (1H, d, J=1.6 Hz), 4.41 (2H, q, J=6.8 Hz), 1.41 (3H, t, J=6.8 Hz).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. customPOCl3 was removed under vacuum
  3. additionThe residue was poured onto ice-water
  4. extractionThe aqueous solution was extracted with CH2Cl2
  5. washThe organic layer was washed with saturated sodium carbonate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-180cb910c93b44ca81223c83f44f51a6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987268B2

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