Sodium Carbonate → HCID 69059825, compound

Participants

Reaction Conditions

Reaction Steps

2.37 g (14.62 mmol) CDI was added to a suspension of 1.9 g (4.87 mmol) of 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]benzo[b]thiophene-2-carboxylic acid in 40 mL of DMF and the reaction mixture was heated to 50° C. overnight. After cooling to RT, the reaction solution was added to a solution of 552 mg (14.62 mmol) NaBH4 in 5 mL of water in such a way that the temperature did not exceed 30° C. The mixture was stirred for 2 hours at RT, carefully mixed with KHSO4 solution until an acidic reaction was obtained, made basic with saturated sodium carbonate solution, extracted exhaustively with DCM, the combined organic phases were washed twice with water and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was triturated with PE, suction filtered, and dried in the air. Yield: 1.1 g (60% of theoretical); C22H14ClNOS (M=375.871); calc.: molpeak (M+H)+: 376/378 (Cl); found: molpeak (M+H)+: 376/378 (Cl); HPLC-MS: 6.2 minutes (method B).

Provenance & Evidence