2-(Tributylstannyl)pyridine → HCID 66844763, compound

Participants

Reaction Steps

A solution of methyl 5-bromo-6-(cyclopentyloxy)nicotinate (4.53 g, 15.1 mmol) and 2-(tributylstannyl)pyridine (5.00 g, 13.6 mmol) was stirred in 100 mL of DMF at 120° C. for 6 h. The resulting solution was cooled and concentrated in vacuo. The crude reaction mixture was then partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted 1×EtOAc. The organic phases were combined, washed 3× brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was taken up in CH2Cl2 and loaded on to a 40 g pre-packed silica gel column. Elution with 0-30% EtOAc:hexanes provided the title compound as an off-white powder (1.71 g, 38%). MS m/z: 299 (M+1).

Provenance & Evidence