Dichloromethane → HCID 16654977、化合物

温度

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レコード

ord-a13414957ad04710a751806ecd0a9f73

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08877923B2