Dichloromethane → HCID 16654977, compound

HRID 537948Notes

Reaction equation

HRID 537948 reaction equation
[CH3:1][C:2]1([CH3:24])[O:6]/[C:5](=[C:7]2/[C:8](=[O:17])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12](I)[CH:11]=3)/[CH:4]=[C:3]1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[C:25]([O:34][CH3:35])(=[O:33])[C:26]1[C:27](=[CH:29][CH:30]=[CH:31][CH:32]=1)[SH:28].C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[CH3:1][C:2]1([CH3:24])[O:6]/[C:5](=[C:7]2/[C:8](=[O:17])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([S:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[C:25]([O:34][CH3:35])=[O:33])[CH:11]=3)/[CH:4]=[C:3]1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 58926149HCID 58926149, compound

Product 1

HCID 16654977HCID 16654977, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-13451ad5fe4e446a9d937dc46ce5eec6
Source dataset
uspto-grants-2014_10
Patent number
US08865682B2

Reaction notes

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