Lithium Chloride → HCID 22316978, compound

HRID 497196Notes

Reaction equation

HRID 497196 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[O:30][CH:31]=[CH:32][CH:33]=1)CCC.[Li+].[Cl-]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 22316717HCID 22316717, compound

Product 1

HCID 22316978HCID 22316978, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-(4-bromophenyl)-4-methyl-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole (0.1 g, 0.26 mmol) in dioxane (5 mL) was added 2-(tributylstannyl)furan (0.118 g, 0.33 mmol), LiCl (0.027 g, 0.64 mmol), tetrakis(triphenylphosphine)palladium(0) (0.03 g, 0.026 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 0.5 hours. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from CH2Cl2/hexane to give the title compound (0.026 g, 26.5% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 0.5 hours
  3. temperatureAfter cooling
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with hexane/ethyl acetate (4/1)
  7. customThe resulting solid was recrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-6bd43b69bc8c41eba5fde9fbad63ba8b
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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