Water → Methyl [2,2'-bipyridine]-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence