Methanol → HCID 178497324, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide from Preparation No. 4 (30.0 g), Et3N (19.1 mL), MeOH (110.6 mL), Pd(OAc)2 (431 mg), and 1,3-bis (diphenylphosphino) propane (791.9 mg) in 375 mL anhydrous DMF is stirred at room temperature until everything dissolves. CO(g) is slowly bubbled through for 2 days and the reaction is maintained at 70° C. The reaction is cooled to room temperature. The product is precipitated by adding 160 mL 1N HCl to the reaction mixture. An orange solid precipitates and is collected. The solid is triturated with EtOAc, filtered, and washed with CH2Cl2 to afford 23.8 g (93%) of the title compound as an off-white solid.

Provenance & Evidence