Sodium Bicarbonate → HCID 15908404, compound

HRID 497186Notes

Reaction equation

HRID 497186 reaction equation
[CH3:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[C:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1.[S:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.C([O-])(O)=O.[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][C:20]([C:26]3[CH:27]=[CH:28][S:24][CH:25]=3)=[CH:19][CH:18]=2)[C:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acidHCID 223168431-(4-Bromophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole

Product 1

HCID 15908404HCID 15908404, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 2-methyl 5-[4-(methylsulfonyl)phenyl]-1-(4-bromophenyl)-1H-pyrrole (0.2 g, 0.51 mmol) in DME (6 mL) was added thiophene-3-boronic acid (0.079 g, 0.61 mmol), bis(triphenylphosphine)palladium(II)chloride (0.04 g, 0.06 mmol) and saturated NaHCO3 solution (2 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 6 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (4/1). The resulting solid was recrystallized from ethyl acetate/hexane to give the title compound (0.15 g, 75.0% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 6 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additionthe filtrate was poured into water
  5. extractionthe whole was extracted with ethyl acetate (10 mL×3)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with hexane/ethyl acetate (4/1)
  11. customThe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0eca0b5b74074b4cbb4177dc267d5e8c
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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