Methyl p-toluenesulfonate → 5-iodo-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 384303Notes

Reaction equation

HRID 384303 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([I:12])[NH:8][C:7]=1[CH3:13])=[O:5])[CH3:2].[CH3:14]OS(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[Na+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([I:12])[N:8]([CH3:14])[C:7]=1[CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 224708Ethyl 5-iodo-2,4-dimethyl-1H-pyrrole-3-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 126042335-iodo-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Iodo-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6d (4.1 g, 13.99 mmol) was dissolved in 80 mL of tetrahydrofuran followed by addition of 4-methyl-benzenesulfonic acid methyl ester (2.73 g, 14.69 mmol) and sodium tert-butoxide (2.02 g, 20.99 mmol). Upon completion of the addition, the reaction mixture was stirred for 0.5 hours and monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure to obtain the title compound 5-iodo-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6e (3.8 g, yield 88.6%) as a grey solid.

Workup

  1. additionUpon completion of the addition
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a31859f65e404e2ba488c0e110cc683a
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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