N-methyl-2-pyrrolidone → HCID 10466854, compound

Participants

Reaction Conditions

Reaction Steps

A solution of BuLi (16.9 mmol) in hexanes (1.6 M, 10.6 ml) was added to a stirred solution of 2,5-dibromopyridine (40 g, 16.9 mmol) in Et2O (300 ml) at −78° C. under N2. The resulting suspension was then stirred at −78° C. for 1 h. N-Methyl pyrrolidinone (1.62 ml, 16.9 mmol) was added and the reaction allowed to warm slowly to room temperature and then stirred at RT for a further 1 h. NH4Cl solution (50 ml) was added and the organics were extracted with Et2O (3×100 ml). The combined organics were washed with brine (50 ml) and then concentrated under reduced pressure. The crude residue was taken up in 1,2-dichloroethane (50 ml), sodium triacetoxyborohydride (3.94 g, 16.9 mmol) was added portionwise and then the reaction mixture was stirred at room temperature overnight. 2 N NaOH solution (50 ml) was added and the organics were extracted with CH2Cl2 (3×100 ml), dried (MgSO4), and concentrated under reduced pressure. The resulting crude residue was purified by column chromatography on silica using 3% MeOH/CH2Cl2 containing 1% NH3 to yield the desired pyridine (480 mg, 10%). m/z (ES+) 241, 243 (1:1, M+H+).

Provenance & Evidence