N-Iodosuccinimide → ethyl 5-iodo-4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate

HRID 1582655Notes

Reaction equation

HRID 1582655 reaction equation
[CH:1]([C:4]1[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH3:9])[NH:7][CH:8]=1)([CH3:3])[CH3:2].[I:15]N1C(=O)CCC1=O>ClCCl>[I:15][C:8]1[NH:7][C:6]([CH3:9])=[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 22718465HCID 22718465, compound

Product 1

HCID 22718488ethyl 5-iodo-4-isopropyl-2-methyl-1H-pyrrole-3-carboxylateYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.03 g of ethyl 4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate in 27 ml of anhydrous dichloromethane was treated with 2.06 g of N-iodosuccinimide and stirred at room temperature for 2 h. The mixture was diluted with a further 50 ml of dichloromethane and washed with 50 ml of saturated sodium thiosulphate solution and 50 ml of saturated sodium hydrogen carbonate solution. The dichloromethane extract was dried over anhydrous sodium sulphate then filtered and evaporated. The residue was triturated with 50 ml of petroleum ether (bp 40-60° C.). The orange solid product was filtered off and dried to give 1.32 g of ethyl 5-iodo-4-isopropyl-2-methyl-1H-pyrrole-3-carboxylate; mass spectrum (ESI) m/z 322 [M+H]+.

Workup

  1. washwashed with 50 ml of saturated sodium thiosulphate solution and 50 ml of saturated sodium hydrogen carbonate solution
  2. extractionThe dichloromethane extract
  3. dry with materialwas dried over anhydrous sodium sulphate
  4. filtrationthen filtered
  5. customevaporated
  6. customThe residue was triturated with 50 ml of petroleum ether (bp 40-60° C.)
  7. filtrationThe orange solid product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-f2fcbc70f9fb47da8d45ff33be8505d6
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

Loading…