Water → 2-[(2-Bromo-3-quinolinyl)methyl]-7-hydroxy-6,7-dihydro-1h-cyclopenta[c]pyridine-1,5(2h)-dione

Participants

Reaction Conditions

Reaction Steps

0.6 mmol (18 mg) of NaH as an 80% dispersion in mineral oil is added in small fractions to a solution, stirred at 0° C. of 0.6 mmol (100 mg) of the compound described in Preparation A in 20 ml of a DME/DMF mixture (16/4 (v/v)). The mixture is stirred at 0° C. for 10 minutes before the addition, at that temperature, of 2.4 mmol (210 mg) of LiBr. After returning to room temperature, the reaction mixture is stirred for ¼ hour before the addition of 0.66 mmol (200 mg) of 2-bromo-3-bromomethylquinoline. The reaction mixture is then heated at 80° C. for 20 hours and, after returning to room temperature, subsequently poured into a large excess of water. The precipitate that forms is filtered off and washed with ether to yield the expected product.

Provenance & Evidence