Pyrrole → HCID 59430825, compound

HRID 1883188Notes

Reaction equation

HRID 1883188 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C[Mg]Br.N1C=CC=CC=1S[C:16]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=[O:17].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[CH3:25][O:24][C:22]([C:21]1[CH:26]=[CH:27][C:18]([C:16]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)=[O:17])=[CH:19][CH:20]=1)=[O:23]

Participants

8

Reactant 4

HCID 8027PyrroleHCID 25517Ammonium ChlorideHCID 23510359HCID 23510359, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59430825HCID 59430825, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-65 °C

Procedure

To a solution of pyrrole (1.68 g) in toluene (40 mL) was added dropwise methyl magnesium bromide in THF (0.93N solution, 27.8 mL) at −20 to −30° C. After the addition, the reaction solution was further stirred for 30 minutes. A solution of methyl 4-[(2-pyridylsulfanyl)-carbonyl]benzoate (8.33 mmol) in toluene (80 mL) was cooled to −78° C., and thereto was added dropwise the above toluene solution via a cannula in such a manner that the temperature of the reaction mixture was not raised over −65° C. After the addition, the reaction solution was stirred at −78° C. for 2 hours, and thereto was added a saturated aqueous ammonium chloride solution (50 mL), and the mixture was warmed to room temperature. To the reaction solution was added ethyl acetate (100 mL), and the organic layer was separated. Further, the aqueous layer was extracted with ethyl acetate (50 mL×2). The organic layers were combined, and washed successively with 9% hydrochloric acid (100 mL), 10% aqueous sodium hydrogen carbonate solution (100 mL), water (100 mL) and a saturated brine (100 mL), dried over magnesium sulfate, filterd and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→4/1) to give the title compound (1.40 g) as colorless solid.

Workup

  1. additionAfter the addition
  2. additionAfter the addition
  3. stirringthe reaction solution was stirred at −78° C. for 2 hours
  4. temperaturethe mixture was warmed to room temperature
  5. customthe organic layer was separated
  6. extractionFurther, the aqueous layer was extracted with ethyl acetate (50 mL×2)
  7. washwashed successively with 9% hydrochloric acid (100 mL), 10% aqueous sodium hydrogen carbonate solution (100 mL), water (100 mL)
  8. dry with materiala saturated brine (100 mL), dried over magnesium sulfate, filterd
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1→4/1)

Sources & evidence

ORD record
ord-954f82311c534496bdeb2592cf95d38a
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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