1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → HCID 67179958, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of LiHMDS (1M in THF, 9.6 mL) was added at −78° C. a solution of (7-fluoro-2-methoxy-quinolin-8-yl)-acetic acid methyl ester (2.0 g, 8.0 mmol; prepared as in WO 2007/081597) in THF (16 mL) over 10 min. After stirring the resulting orange mixture for 1 h at −78° C., a solution of N-(bromomethyl)phthalimide (1.2 eq.) in THF (16 mL) was added dropwise over 10 min. The mixture was stirred 1 h at −78° C. and then at rt overnight. The yellow solution was quenched with 1N HCl (80 mL) and then extracted with DCM. The combined org layers were washed with water, dried over MgSO4, concentrated and purified by CC (Hept/EA 1:1) to give 1.89 g of a yellow solid which was recrystallized from EA/MeOH/NH4OH (90:10:1) to afford the title intermediate as a colourless solid (924 mg, 28% yield).

Provenance & Evidence