Dimethyl Sulfoxide → HCID 67538041, compound

HRID 2240987Notes

Reaction equation

HRID 2240987 reaction equation
[CH:1]1([CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][CH:16]=3)[CH:8]=2)[F:6])[CH2:3][CH2:2]1.CS(C)=[O:27].[OH2:29]>CC#N.CC#N.Cl[Pd]Cl>[CH:1]1([CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([C:13](=[O:27])[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:17][CH:16]=3)=[O:29])[CH:10]=[CH:11][CH:12]=2)[F:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 67537665HCID 67537665, compound

Product 1

HCID 67538041HCID 67538041, compound

Reagents, catalysts & solvents 1

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst

Conditions

Temperature
145 °C

Procedure

A mixture of 1-(2-cyclopropyl-1-fluorovinyl)-3-{[4-(difluoromethoxy)phenyl]ethynyl}benzene (0.1 g, 0.3 mmol) and DMSO (1 mL) was degassed with argon for 5 minutes. Then, bis(acetonitrile)dichloropalladium (II) (7.8 mg, 0.03 mmol) was added and the mixture was stirred at 145° C. for 8 hours. Then, the mixture was poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by ICSO (hexane/EtOAc 4/1) gave 1-[3-(2-cyclopropyl-1-fluorovinyl)phenyl]-2-[4-(difluoromethoxy)phenyl]ethane-1,2-dione 1:1 Z/E isomers (78 mg); MS m/e (M)+ 360.

Workup

  1. customwas degassed with argon for 5 minutes
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by ICSO (hexane/EtOAc 4/1)

Sources & evidence

ORD record
ord-103a8517ad1e4ce4816d05f02c61ba1f
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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