Potassium Phosphate, Tribasic → HCID 86654667, compound

HRID 880446Notes

Reaction equation

HRID 880446 reaction equation
[CH:1]([C:3]1[N:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6](I)[CH:7]=1)=[O:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=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>[CH:1]([C:3]1[N:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=1)=[O:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86654666HCID 86654666, compound

Product 1

HCID 86654667HCID 86654667, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of ethyl 2-(2-formyl-4-iodo-pyrrol-1-yl)acetate (3.0 g, 9.77 mmol) in dimethylformamide (25 mL) was purged with argon gas for 10 min. Bis-(triphenylphosphine)-palladium(II) chloride (0.48 g, 0.68 mmol) was added and the mixture was purged with argon gas for 5 min. Anhydrous potassium phosphate (6.18 g, 29.3 mmol) and phenylboronic acid (1.43 g, 11.7 mmol) were added successively and the reaction mixture purged with argon gas for 10 min, then heated to 110° C. and maintained at that temperature for 4 h. The resulting mixture was allowed to cool to ambient temperature and diethyl ether added. The reaction mixture was filtered, the filtrate being washed with water and the separated aqueous phase being further extracted with diethyl ether. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product. Purification by column chromatography over silica gel (100-200 mesh) using 8% ethyl acetate in petroleum ether as eluent afforded ethyl 2-(2-formyl-4-phenyl-pyrrol-1-yl)acetate (680 mg, 27%).

Workup

  1. customthe mixture was purged with argon gas for 5 min
  2. customthe reaction mixture purged with argon gas for 10 min
  3. temperaturemaintained at that temperature for 4 h
  4. temperatureto cool to ambient temperature
  5. additiondiethyl ether added
  6. filtrationThe reaction mixture was filtered
  7. washthe filtrate being washed with water
  8. extractionthe separated aqueous phase being further extracted with diethyl ether
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto afford the crude product
  14. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-ab7a1932c392415fae8d66f0fc7c10a6
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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