Reaktion #316800

Reaktionsgleichung

NaHCO3

lithium hydride

EtOAc

4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde

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title compound

Ausbeute 89.0%

ethyl (2E)-3-[4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]acrylate

Ausbeute 89.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux for 2 h
3. 3
   TemperaturAfter it was cooled to rt
4. 4
   SonstigeThe organic layer was collected
5. 5
   Extraktionthe aqueous layer was back extracted with EtOAc (2×)
6. 6
   TrocknenThe combined organic layers were dried (Na2SO4)
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto give a crude yellow solid
9. 9
   Sonstigethat was purified by column chromatography (10:90 to 90:10 v/v EtOAc-hexanes)

Vorschrift

To a suspension of lithium hydride (68 mg, 4.0 mmol) in THF (5 mL) under N2 atmosphere was added triethyl phosphonoacetate (498 mg, 2.22 mmol). The mixture was stirred at rt for 30 min and to the reaction mixture was added a slurry of 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde (433 mg, 1.53 mmol) in THF (15 ml). The mixture was heated at reflux for 2 h. After it was cooled to rt, aqueous NaHCO3 was slowly added followed by EtOAc. The organic layer was collected and the aqueous layer was back extracted with EtOAc (2×). The combined organic layers were dried (Na2SO4) and evaporated to give a crude yellow solid that was purified by column chromatography (10:90 to 90:10 v/v EtOAc-hexanes) to afford the title compound (480 mg, 89%). 1H-NMR (CD3OD) δ 8.42 (d, J=8.0 Hz, 2H), 8.17 (s, 1H), 7.88 (s, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.43 (d, J=16 Hz, 1H), 6.36 (d, J=16 Hz, 1H), 4.16 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3H); MS [M+H]+=354; LCMS RT=3.12 min.

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