3-Bromoquinoline → HCID 18518589, compound

Participants

Reaction Steps

To 3-bromoquinoline (56.3 mg, 1.1 eq) in anhydrous Et2O (1.0 mL) at −50° C. (internal temperature) and under a nitrogen atmosphere was added n-BuLi (0.18 mL, 1.1 eq, 1.53 M in hexanes). Stirring was continued for minutes and then to the resulting red/brown coloured precipitate was added 1-(2-diethylaminoethyl)-4-bromoisatin (80.0 mg, 2.46×10−4 mol) in anhydrous Et2O (2.0 mL) and the resulting dark blue coloured mixture was stirred for a further 8.5 hours at −50° C. Saturated aqueous NH4Cl (1.5 mL) was added and the mixture 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 flash chromatography (silica gel, eluting 2% MeOH in CHCl3) to yield the title compound as a yellow oil (5.3 mg, 5%).

Provenance & Evidence