Isopropyl iodide → Methyl 1-isopropyl-1H-pyrrole-3-carboxylate

HRID 2204301Notes

Reaction equation

HRID 2204301 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][NH:9][CH:8]=1)=[O:6].I[CH:13]([CH3:15])[CH3:14]>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][N:9]([CH:13]([CH3:15])[CH3:14])[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 86703103Methyl 1-isopropyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (58.1 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid methyl ester [2703-17-5] (38.8 mmol) in DMF (80 mL) at 0° C. and the mixture was stirred for 1.5 h. 2-Iodo-propane (78 mmol) was added and the mixture was stirred at rt for 4 h. The reaction mixture was quenched with 1N aqueous KHSO4 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as an orange-brown oil. tR: 3.80 min (HPLC 1); ESI-MS: tR=0.92 min, [M+H]+ 168 (LC-MS 1); TLC: Rf=0.22 (1:6 EtOAc/heptanes).

Workup

  1. stirringthe mixture was stirred at rt for 4 h
  2. customThe reaction mixture was quenched with 1N aqueous KHSO4
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-ba029ebf06da41e59a6622122c7adde6
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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