Reacción #70146

Ecuación de reacción

2-Chloro-3-pyridinecarboxaldehyde

4-fluorobenzenesulfinic acid sodium salt

→

desired product

2-(4-Fluorobenzenesulfonyl)-pyridine-3-carboxaldehyde

Disolventes

water

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaUpon cooling to ambient the mixture
2. 2
   Extracciónextracted with EtOAc (3×)
3. 3
   LavadoThe combined organics were washed with water, brine
4. 4
   Secadodried (MgSO4)
5. 5
   Otroevaporated to dryness
6. 6
   Otroto afford 7.89 g of crude product
7. 7
   OtroThe crude compound was pre-absorbed onto silica
8. 8
   Otropurified
9. 9
   Otroby dry pad suction column chromatography
10. 10
    Lavadoeluting with heptane using an EtOAc gradient

Procedimiento

2-Chloro-3-pyridinecarboxaldehyde (4.04 g, 2.86 mmol) and 4-fluorobenzenesulfinic acid sodium salt (5.73 g, 3.14 mmol) were dissolved in DMSO (100 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 7.89 g of crude product. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.14 g (41%) of the desired product as a yellow solid (plates) (MP=131-131.3° C.; IR=1691 cm−1; HPLC=7.21 min>99%).

Fuente