Sodium Bicarbonate → 5-[3-Fluoro-4-(methylsulfonyl)phenyl]1-[4-(2-furyl)phenyl]-2-methyl-1H-pyrrole

HRID 396747Notes

Reaction equation

HRID 396747 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[C:16]([F:24])[CH:15]=2)=[CH:4][CH:3]=1.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:24][C:16]1[CH:15]=[C:14]([C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([C:26]4[O:25][CH:29]=[CH:28][CH:27]=4)=[CH:3][CH:4]=3)[C:12]([CH3:13])=[CH:11][CH:10]=2)[CH:19]=[CH:18][C:17]=1[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734357Furan-2-boronic acidHCID 223168021-(4-Bromophenyl)-2-(3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H-pyrrole

Product 1

HCID 159084015-[3-Fluoro-4-(methylsulfonyl)phenyl]1-[4-(2-furyl)phenyl]-2-methyl-1H-pyrroleYield 61%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a stirred suspension of 1-(4-bromophenyl)-2-[3-fluoro-4-(methylsulfonyl)phenyl]-5-methyl-1H -pyrrole (0.41 g, 1 mmol), 2-furanboronic acid (0.14 g, 1.26 mmol), NaHCO3 (0.19 g, 2.3 mmol) in DME-water (6 mL-2 mL) was added dichlorobis(triphenylphosphine)palladium (80 mg, 0.115 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 6 hours. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2) to give the title compound (0.24 g, 61% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 6 hours
  3. temperatureAfter cooling
  4. customvolatiles were removed by evaporation
  5. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record
ord-9b7b02a978154355a1db4a4027627933
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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