3-Bromopyridine → HCID 18518611, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of n-BuLi (0.16 mL, 1.0 eq, 1.53 M in hexanes) at −78° C., in anhydrous Et2O (1.0 mL), and under a nitrogen atmosphere was added a solution of 3-bromopyridine (40.8 mg, 0.0249 mL, 1.05 eq) in anhydrous Et2O (0.5 mL). The resulting light yellow coloured precipitate was stirred at −78° C. for 30 minutes and then a solution of isatin 1-(2-diethylaminoethyl)-4-bromoisatin (80.0 mg, 2.46×10−4), in anhydrous Et2O (1.5 mL) was added dropwise. The solution was stirred for a further 7.5 hours. Saturated aqueous NH4Cl (1.5 mL) was added to the resulting brown coloured reaction mixture and the reaction was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration, the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, 1% to 1.5% to 2% MeOH in CHCl3) to yield the title compound as a light yellow oil (35.5 mg, 36%).

Provenance & Evidence