Sodium Carbonate → Ethyl 5-phenyl-1H-pyrrole-2-carboxylate

HRID 1178113Notes

Reaction equation

HRID 1178113 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH2:7]([O:9][C:10]([C:12]1[NH:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11])[CH3:8].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.O.O.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>[CH2:7]([O:9][C:10]([C:12]1[NH:13][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:11])[CH3:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59559613ethyl 5-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 12378033Ethyl 5-phenyl-1H-pyrrole-2-carboxylateYield 67.95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 22272177Toluene waterSolvent

Procedure

Na2CO3 (97.5 mg, 0.92 mmol) was added to a stirred solution of 5-bromo-1H-pyrrole-2-carboxylic acid ethyl ester (100 mg, 0.46 mmol) in toluene: H2O (5:1, 11 mL). Pd (PPh3)4 (53 mg, 0.046 mmol) and phenylboronic acid (84.3 mg, 0.7 mmol) were then added and the reaction mixture was heated to reflux for 2 hrs. The reaction mixture was then diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated to get the residue. The residue obtained was purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent) afford 67 mg (67.95% yield) of 5-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester. 1H NMR (CDCl3): δ 9.4 (s, 1H), 7.64 (d, 2H), 7.48 (t, 2H), 7.36 (d, 11H), 7.0 (s, 1H), 6.58 (s, 1H), 4.4 (q, 2H), 1.4 (t, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hrs
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto get the residue
  8. customThe residue obtained
  9. customwas purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-18352064f7724b60867a5fb68417d3d0
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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