Pyridine → HCID 12052636, compound

Participants

Reaction Steps

To 4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid (350 mg, 1.29 mmol) in CH2Cl2 (2 ml) was added oxalyl chloride (327 mg, 2.58 mmol) and a catalytic amount of DMF. The mixture was stirred at room temperature for 1 h and then concentrated under reduced pressure. The acid chloride was dried, under vacuum, overnight. To the aniline (Example 1, Part D; 0.49 g, 1.17 mmol), in pyridine (0.158 g, 2.34 mmol) and CH2Cl2 (3 mL) at 0° C. and under N2, was added the previously formed acid chloride (see Example 5, Part D) in 4 mL CH2Cl2 dropwise. Upon completion of addition, the mixture was stirred for 15 minutes at room temperature and then the reaction quenched by the addition saturated NaHCO3. Product was extracted with EtOAc, the organics washed with H2O, and concentrated under reduced pressure; yielding 583 mg of desired product after flash chromatography (SiO2, 10% MeOH in CHCl3).

Provenance & Evidence