4-Cyanobenzoyl chloride → HCID 59556569, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL microwave vial equipped with a stirring bar was charged with 4-cyanobenzoyl chloride (0.4 g, 2.416 mmol), (Z)-3-bromo-N′-hydroxy-4-isopropoxybenzimidamide (0.5 g, 1.831 mmol) and pyridine (15 ml) to give an orange solution. The vessel was capped and the reaction heated at 200° C. for 20 min under microwave irradiation (Biotage Optimizer, 300 W). The solution was cooled, the reaction mixture was partitioned between aqueous HCl (10%, 150 mL) and DCM (40 mL) mixture, the DCM layer was drained, and the aqueous layer was extracted by DCM (2×20 mL). The combined DCM layers were washed by water (2×20 mL) and concentrated to afford white solid, which was purified via silica gel chromatography (40 g, 40% EtOAc:Heptane) to afford 4-(3-(3-bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzonitrile (0.638 g, 1.660 mmol, 91% yield) as white solid. LC/MS (Method c) Rt=3.17 min.; MS m/z: 386.19 (M+H)+. 1H NMR (400 MHz, Solvent d-DMSO) ppm 8.40-8.32 (m, 2H), 8.23 (d, J=2.13 Hz, 1H), 8.14 (dd, J=8.14, 0.61 Hz, 2H), 8.05 (dd, J=8.65, 2.15 Hz, 1H), 7.36 (d, J=9.12 Hz, 1H), 4.89-4.77 (m, 1H), 1.35 (d, J=6.03 Hz, 6H).

Provenance & Evidence