Pyridine → ethyl 1-ethyl-4-[methyl(2-thienylsulfonyl)amino]-1H-pyrrole-2-carboxylate

HRID 453575Notes

Reaction equation

HRID 453575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([CH2:7][CH3:8])[CH:6]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[S:19](Cl)(=[O:21])=[O:20].N1C=CC=C[CH:24]=1>>[CH2:7]([N:5]1[CH:6]=[C:2]([N:1]([CH3:24])[S:19]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)(=[O:21])=[O:20])[CH:3]=[C:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:8]

Participants

4

Reactant 3

HCID 1049PyridineHCID 855182-Thiophenesulfonyl chlorideHCID 59411398ethyl 4-amino-1-ethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 59411397ethyl 1-ethyl-4-[methyl(2-thienylsulfonyl)amino]-1H-pyrrole-2-carboxylateYield 88%

Procedure

To a mixture of ethyl 4-amino-1-ethyl-1H-pyrrole-2-carboxylate (7.1 g) and pyridine (50 mL) was added 2-thiophen-sulfonyl chloride (8.4 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. To a solution of the residue in N,N-dimethylformamide (50 mL) was slowly added sodium hydride (60%, oily, 1.7 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Methyl iodide (2.7 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give ethyl 1-ethyl-4-[methyl(2-thienylsulfonyl)amino]-1H-pyrrole-2-carboxylate (11.9 g, yield 88%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customat 0° C.
  8. stirringthe mixture was stirred at room temperature for 30 min
  9. additionMethyl iodide (2.7 mL) was added to the reaction mixture
  10. stirringthe mixture was stirred at room temperature for 1 hr
  11. additionWater was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated brine
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-9e652bd2dc834a57af900a24b8e423fe
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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