HCID 59556706, compound → HCID 59556666, compound

Temperature

230 °C

A 25 mL microwave vial equipped with a stirring bar was charged with 3-(3-bromo-4-isopropoxyphenyl)-5-(4-(dimethoxymethyl)phenyl)-1,2,4-oxadiazole (0.25 g, 0.577 mmol), copper(I) cyanide (0.133 g, 1.485 mmol) and pyridine (15 ml). The vessel was capped and the reaction heated to 230° C. for 30 min under microwave irradiation (Biotage Optimizer, 300 W). The solution was cooled, the reaction mixture was concentrated, to the residue was added hydrated ferric chloride (0.8 g), concentrated hydrochloric acid (2 mL) and water (12 mL). The solution was heated at 65° C. for 20 min, the aqueous mixture was extracted by DCM (3×30 mL), the combined DCM layers were washed with FeCl3 solution (2×20 mL), then water (2×20 mL), dried (brine, MgSO4) and concentrated to yield yellow solid, which was purified via silica gel chromatography (40 g, 20% EtOAc:Heptane) to afford 5-(5-(4-(dimethoxymethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile (0.086 g, 0.227 mmol, 39.3% yield) as pale yellow solid.

1. customA 25 mL microwave vial equipped with a stirring bar
2. customThe vessel was capped
3. temperatureThe solution was cooled
4. concentrationthe reaction mixture was concentrated, to the residue
5. additionwas added hydrated ferric chloride (0.8 g), concentrated hydrochloric acid (2 mL) and water (12 mL)
6. temperatureThe solution was heated at 65° C. for 20 min
7. extractionthe aqueous mixture was extracted by DCM (3×30 mL)
8. washthe combined DCM layers were washed with FeCl3 solution (2×20 mL)
9. dry with materialwater (2×20 mL), dried (brine, MgSO4)
10. concentrationconcentrated
11. customto yield yellow solid, which
12. customwas purified via silica gel chromatography (40 g, 20% EtOAc:Heptane)

ORD record

ord-8b354f497cf8440daf569c8b5a0a7532

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834039B2