Cyanoacetic acid → HCID 69607335, compound

Participants

Reaction Steps

Cyanoacetic acid (1.2 g, 14.0 mmol) and CH2Cl2 (14 ml) were combined at rt under N2. The solids do not dissolve. PCl5 (2.9 g, 14.0 mmol) was added as a solid portion wise (bubbles vigorously). The suspension was heated at reflux for 30 min and all solids dissolve to give a clear, light yellow solution. The acyl chloride solution was cooled and added directly to 5′-Amino-5-iodo-4-methyl-[2,3′]bithiophenyl-4′-carboxylic acid ethyl ester (2.0 g, 5.1 mmol) in CH2Cl2. The solution was stirred at rt for 2.5 h. The reaction was poured into NaHCO3 (aq, sat.) and washed a second time with NaHCO3 (aq, sat.). The organics were washed with brine and dried (Na2SO4), filtered and concentrated by rotary evaporation to give a light yellow solid which was then triturated with CH3CN and filtered to give 5′-(2-Cyano-acetylamino)-5-iodo-4-methyl-[2,3′]bithiophenyl-4′-carboxylic acid ethyl ester (1.7 g, 3.7 mmol) as a white solid. This material was taken to the next step without further purification.

Provenance & Evidence