1-Methanesulfonyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester → 4-Amino-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2249509

Reaction equation

HRID 2249509 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 596396991-Methanesulfonyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 596397164-Amino-1-methanesulfonyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-methanesulfonyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester (2.4 g, 9.15 mmol) in ethanol (30 mL) was added Pd/C (10%) (120 mg) under nitrogen atmosphere. The reaction flask was charged with hydrogen at 50 psi for 2 hours. The catalyst was removed by filtration through celite. The solvent was evaporated under reduced pressure to afford a sticky syrup that was purified by flash column eluting with 50% EtOAc in hexanes to give the product as sticky oil (2.1 g, 99%). MS (ES+): m/e=233.1 (M+H); LC/Method A/2.36 min.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customto afford a sticky syrup that
  4. customwas purified by flash column
  5. washeluting with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-ebd68d00c4914b5d929ef81a58545703
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Linked notes

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