Diiodomethane → Ethyl 4-cyano-3-iodo-1-methyl-1H-pyrrole-2-carboxylate

HRID 1865045Notes

Reaction equation

HRID 1865045 reaction equation
I[CH2:2][I:3].[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:17])[CH:11]=[C:12](C#N)[C:13]=1[NH2:14])=[O:8])[CH3:5].C(ON=O)CC(C)C>C(#N)C>[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:17])[CH:11]=[C:12]([C:13]#[N:14])[C:2]=1[I:3])=[O:8])[CH3:5]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 902351ethyl 3-amino-4-cyano-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 57974967Ethyl 4-cyano-3-iodo-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add diiodomethane (22.15 mL, 274.97 mmol) to 3-amino-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (14.75 g, 76.34 mmol, prepared in preparation 33) in acetonitrile with stirring at room temperature. Next, add isoamylnitrite (25.65 mL, 190.92 mmol) while heating the reaction to 35° C. After complete addition, the reaction is heated to 65° C. After 10 minutes; cool the reaction mixture to room temperature and concentrate under reduced pressure. Purify the residue by filtering over silica gel with methylene chloride and triturating the filtrate with hexane to afford the title compound.

Workup

  1. temperaturewhile heating
  2. customthe reaction to 35° C
  3. additionAfter complete addition
  4. temperaturethe reaction is heated to 65° C
  5. temperaturecool the reaction mixture to room temperature
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue
  8. filtrationby filtering over silica gel with methylene chloride
  9. customtriturating the filtrate with hexane

Sources & evidence

ORD record
ord-240aa296cb594ceab6d3a12bda0cd437
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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