Ethyl Acetate → HCID 71269701, compound

Participants

Reaction Steps

To a solution of carboxylic acid (200 mg, 1.3 mmol) and DMF (1 drop) in EtOAc (5 mL) was added oxalyl chloride (0.3 mL, 3.45 mmol) at room temperature. The reaction was stirred for 2 h and the volatiles were removed in vacuo. A solution of 5-(3,3-dimethylbut-1-ynyl)-N-isopropylthiophen-3-amine (170 mg, 0.77 mmol) and DIEA (0.3 mL) in DCE (1 mL) was then added. The reaction was stirred overnight. The mixture was poured into EtOAc (150 mL), and the organics were washed with saturated NaHCO3 (2×50 mL) and brine (50 mL). After drying over Na2SO4, the organic layer was concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexanes) to give the desired product (116 mg, 25% yield) as a dark oil.

Provenance & Evidence