Ethyl Acetate → HCID 52952224, compound

HRID 1784874Notes

Reaction equation

HRID 1784874 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[CH:10]=[C:11]([SH:16])[CH:12]=[C:13]([Cl:15])[CH:14]=1.CC(C)([O-])C.[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([S:16][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 707143-IodopyridineHCID 27360963,5-DichlorobenzenethiolHCID 23665647Potassium tert-butoxide

Product 1

HCID 52952224HCID 52952224, compoundYield 717.1%

Reagents, catalysts & solvents 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.018 g (0.020 mmol) Pd2dba3 and 0.021 g (0.039 mmol) DPEphos in toluene (3 mL) was stirred under an argon atmosphere for 5 minutes. 3-Iodo-pyridine (0.100 g, 0.49 mmol), 3,5-dichlorobenzenethiol (0.087 g, 0.49 mmol) and 0.060 g (0.54 mmol) potassium t-butoxide were added and the reaction mixture was heated to 100° C. and held for 2 hours, then cooled. Ethyl acetate was added to the reaction mixture and the organic phase was washed with water, dried and concentrated. The crude product was purified using flash chromatography to give 0.90 g (72% yield) 3-(3,5-dichloro-phenylsulfanyl)-pyridine.

Workup

  1. temperaturecooled
  2. washthe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-fe53dbf2e3084c29a53f43c3f3606311
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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