Sodium Bicarbonate → HCID 22316823, compound

HRID 2086646Notes

Reaction equation

HRID 2086646 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=2)[N:6]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.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[O:3][C:4]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:9][CH:8]=2)[N:6]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 223167672-Methyl-5-[4-(methylsulfonyl)phenyl]-4-(4-bromophenyl)-oxazole

Product 1

HCID 22316823HCID 22316823, compoundYield 71.2%

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 2-methyl-5-[4-(methylsulfonyl)phenyl]-4-(4-bromophenyl)-oxazole (0.314 g, 0.8 mmol) in DME (10 mL) was added thiophene-2-boronic acid (0.123 g,0.96 mmol), bis(triphenylphosphine)palladium(II)chloride (0.064 g, 0.09 mmol) and saturated NaHCO3 solution (3.2 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 4.5 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 (3/2). The resulting solid was recrystallized from ethyl acetate/hexane to give the title-compound (0.225 g, 71.2% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4.5 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 (3/2)
  11. customThe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d1df23524b574abb9ce88480ab90f48c
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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