Iodoethane → 1-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrrole

HRID 646253Notes

Reaction equation

HRID 646253 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([S:7]([CH3:10])(=[O:9])=[O:8])[NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17](I)[CH3:18]>CN(C=O)C.CCOC(C)=O>[CH2:17]([N:5]1[CH:6]=[C:2]([I:1])[CH:3]=[C:4]1[S:7]([CH3:10])(=[O:9])=[O:8])[CH3:18]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 597726954-iodo-2-methanesulfonyl-1H-pyrrole

Product 1

HCID 597727121-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrroleYield 10%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-iodo-2-methanesulfonyl-1H-pyrrole (0.14 g, 0.52 mmol) in DMF was treated with Cs2CO3 (0.84 g, 2.58 mmol) and ethyl iodide (0.161 g, 1.03 mmol). The reaction mixture was diluted with EtOAc and washed sequentially with water and brine. The organic phase was separated, dried (Na2SO4) and concentrated in vacuo. Chromatography of the resultant residue (silica gel, 10%-30% EtOAc-hexanes as eluent) yielded an oil; 1H NMR (400 MHz, CDCl3) δ: 1.47 (t, 3H, J=7.3 Hz), 3.09 (s, 3H), 4.26 (q, 2H, J=7.3 Hz), 6.90 (m, 1H), 6.95 (s, 1H).

Workup

  1. washwashed sequentially with water and brine
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5ac1c5f2e3045679f5546edb5dc95d7
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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