Reaktion #603767

Reaktionsgleichung

Dimethyl(1-diazo-2-oxopropyl)phosphonate

methyl 4-amino-5-fluoro-6-(4-formylphenyl)-3-vinylpicolinate

potassium carbonate

MeOH

→

title compound

Ausbeute 61.8%

methyl 4-amino-6-(4-ethynylphenyl)-5-fluoro-3-vinylpicolinate

Ausbeute 61.8%

Lösungsmittel

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 20 mL reaction
2. 2
   Waschenwashed with a 5% solution of NaHCO3 (25 mL) The organic layer
3. 3
   Trocknenwas dried over MgSO4 (5 g)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated on a rotary evaporator
6. 6
   SonstigeThe resulting reside was purified
7. 7
   Sonstigea Teledyne ISCO purification system with a gradient eluent system of CH2Cl2 and EtOAc

Vorschrift

To a 20 mL reaction vial was added methyl 4-amino-5-fluoro-6-(4-formylphenyl)-3-vinylpicolinate (0.41 g, 1.365 mmol), potassium carbonate (0.377 g, 2.73 mmol) and MeOH (10 mL). Dimethyl(1-diazo-2-oxopropyl)phosphonate (0.315 g, 1.638 mmol) was added in one portion. After stirring for 4 h, the reaction mixture was diluted with Et2O (50 mL) and washed with a 5% solution of NaHCO3 (25 mL) The organic layer was dried over MgSO4 (5 g), filtered, and concentrated on a rotary evaporator. The resulting reside was purified using a Teledyne ISCO purification system with a gradient eluent system of CH2Cl2 and EtOAc to yield the title compound as a white solid (250 mg).

Quelle