Methyl iodide → methyl 5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1518714Notes

Reaction equation

HRID 1518714 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:10]([CH3:12])[CH:11]=1)=[O:6].[CH3:20]I>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH3:20])[C:9]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:10]([CH3:12])[CH:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68286466methyl 5-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 68286033methyl 5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylateYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of sodium hydride (60% suspension in mineral oil) (0.529 g, 13.22 mmol) in DMF (5 ml) at 0° C. was added a solution of methyl-5-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (prepared according to the procedure reported in J. org. Chem., 2009, 74(2), 903-905, Org. Lett. 2007, 9(25), 5191-5194, 2.20 g, 8.81 mmol) in DMF (10 ml), which was then followed by the addition of methyl iodide (1.88 g, 0.83 ml, 13.22 mmol). The resulting reaction mixture was stirred at room temperature for 45 minutes. The progress of the reaction was monitored by TLC. The reaction mixture was then quenched with water (10 ml). The mixture so obtained was then extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 15-20% ethyl acetate in hexanes as an eluent to obtain the title compound (1.9 g, 81.9%)

Workup

  1. customprepared
  2. customThe resulting reaction mixture
  3. customThe reaction mixture was then quenched with water (10 ml)
  4. customThe mixture so obtained
  5. extractionwas then extracted with ethyl acetate (2×50 ml)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. customThe solvent was evaporated from the dried organic layer under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-e841f23e5e66430eb798a20408f5f1d2
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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