Dichloromethane → HCID 16654977, Verbindung

Temperatur

90 °C

A 25 mL reaction vessel was charged with (3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-6-iodo-1,3-dihydro-2H-indol-2-one (100 mg, 0.23 mmol), methyl thiosalicylate (77 mg, 0.46 mmol), PdCl2(dppf).CH2Cl2 (19 mg, 0.023 mmol), cesium carbonate (225 mg, 0.69 mmol) and 8 mL of anhydrous DMF. The mixture was purged with nitrogen and heated in 90° C. bath for 2.5 hours. The mixture was cooled to room temperature, diluted with 50 mL of water and extracted with EtOAc (3×50 mL). The organic layers were combined, washed with saturated NaHCO3 (50 mL), brine (2×50 mL), dried over Na2SO4, and concentrated to give a brown oil. Purification of the oily mixture by silica gel chromatography eluted with 1-10% MeOH/CHCl3 provided methyl 2-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]thio}benzoate as a brown solid. Yield: 60 mg, 55%.

1. customA 25 mL reaction vessel
2. customThe mixture was purged with nitrogen
3. temperatureThe mixture was cooled to room temperature
4. additiondiluted with 50 mL of water
5. extractionextracted with EtOAc (3×50 mL)
6. washwashed with saturated NaHCO3 (50 mL), brine (2×50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customto give a brown oil
10. customPurification of the oily mixture by silica gel chromatography
11. washeluted with 1-10% MeOH/CHCl3

ORD-Eintrag

ord-13451ad5fe4e446a9d937dc46ce5eec6

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08865682B2