Reacción #681419

Ecuación de reacción

methyl 2-chloroisonicotinate

2-(trimethylstannyl)pyridine

water

AcOEt

→

methyl[2,2′-bipyridine]-4-carboxylate

Disolventes

meta-xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to rt
2. 2
   ExtracciónThe separated aq. layer was further extracted with AcOEt
3. 3
   LavadoThe mixed organic layers were washed with brine
4. 4
   Secadodried over anh. MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated to dryness under reduced pressure
7. 7
   OtroPurification by FC (DCM/MeOH=15/1)

Procedimiento

A mixture of commercially available methyl 2-chloroisonicotinate (300 mg; 1.74 mmol), 2-(trimethylstannyl)pyridine (422 mg; 1.74 mmol), and PdCl2(PPh3)2 (122 mg; 0.17 mmol) in anh. meta-xylene (7 ml) was heated to 75° C., under nitrogen, for 18 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl[2,2′-bipyridine]-4-carboxylate as a yellow solid. LC-MS (conditions A): tR=0.46 min.; [M+H]+: 215.15 g/mol.

Fuente