Dimethyl Sulfoxide → HCID 59772717, compound

HRID 646267Notes

Reaction equation

HRID 646267 reaction equation
CS(C)=O.[Br:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][C:14]2[CH:15]=[C:16]([CH:19]=[O:20])[NH:17][CH:18]=2)[CH:9]=[CH:10][CH:11]=1.C(OCC)(=[O:23])C.[OH2:27]>[Pd](Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([C:12](=[O:23])[C:13]([C:14]2[CH:15]=[C:16]([CH:19]=[O:20])[NH:17][CH:18]=2)=[O:27])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8857Ethyl AcetateHCID 59772707HCID 59772707, compound

Product 1

HCID 59772717HCID 59772717, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
140 °C

Procedure

To DMSO was added 4-[(3-bromophenyl)ethynyl]-1H-pyrrole-2-carbaldehyde (1.50 g; 5.47 mmol), and palladium(II) chloride (97 mg; 0.547 mmol). The resulting solution was stirred at 140° C. for one hour. The mixture was cooled to ambient temperature and diluted with water. The product was extracted into chloroform and dried over MgSO4. The resulting solid was chromatographed on silica gel using 7:3 hexane:ethyl acetate to give 1.21 g of the title compound as a greenish crystalline solid (72% yield), mp 202-203° C.; MS (ES) m/z 304.0, [M−H]−.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionThe product was extracted into chloroform
  3. dry with materialdried over MgSO4
  4. customThe resulting solid was chromatographed on silica gel using 7:3 hexane

Sources & evidence

ORD record
ord-f3c30906818942629f237f9708a4bd4d
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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