4-Toluenesulfonyl chloride → Methyl 4-iodo-1-tosyl-1H-pyrrole-2-carboxylate

HRID 1479146Notes

Reaction equation

HRID 1479146 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4].C(N(CC)CC)C.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

Product 1

HCID 59694429Methyl 4-iodo-1-tosyl-1H-pyrrole-2-carboxylateYield 75.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Iodo-1H-pyrrole-2-carboxylic acid methyl ester (24.6 g, 98 mmol, 1.0 equivalent) was dissolved in dichloromethane (150 mL) and triethylamine (30 mL, 215.6 mmol, 2.2 equivalents). 4-(Dimethylamino)pyridine (1.2 g, 9.8 mmol, 0.1 equivalent) and p-toluenesulfonylchloride (20.6 g, 107.8 mmol, 1.1 equivalents) were added and the reaction mixture was stirred for 16 hours at room temperature. The reaction was quenched with 1 M HCl and the organic layer was washed with aqueous sodium bicarbonate and brine. After drying over magnesium sulfate, the solvent was removed under reduced pressure and the residue was crystallized from tert-butylmethyl ether, yielding the title compound as a pale yellow solid (30 g, 75%). Rt(min) 8.259 minutes.

Workup

  1. customThe reaction was quenched with 1 M HCl
  2. washthe organic layer was washed with aqueous sodium bicarbonate and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was crystallized from tert-butylmethyl ether

Sources & evidence

ORD record
ord-41df2cdc76974d7cb18e351b853017f5
Source dataset
uspto-grants-2016_08
Patent number
USRE046097E1

Reaction notes

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