Methyl iodide → HCID 71203617, compound

HRID 1844557Notes

Reaction equation

HRID 1844557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:11]=2[CH3:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[H-].[Na+].[CH3:22]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14]([CH3:22])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:11]=2[CH3:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71187146HCID 71187146, compound

Product 1

HCID 71203617HCID 71203617, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 5-(3-bromo-4-methoxyphenyl)-4-methyl-1H-pyrrole-2-carboxylate (prepared according to the procedure reported in J. Org. Chem., 2009, 74(2), 903-905, Org. Lett., 2007, Vol. 9, 25, 5191-5194, 1.40 g, 4.32 mmol) in DMF (3 ml) was added to a solution of sodium hydride (0.21 g 60% in paraffin oil, 4.75 mmol) in DMF (2 ml) at 0° C. under stirring. Methyl iodide (0.67 g, 0.29 ml, 4.75 mmol) was then added to the reaction mixture. The reaction mixture was stirred at room temperature for 45 minutes. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with water (5 ml) and 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. The crude product was further purified by flash column chromatography using 20% ethyl acetate in hexanes as an eluent to obtain the title compound 10a (1.25 g, 85%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 45 minutes
  2. customThe reaction mixture was quenched with water (5 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customThe solvent was evaporated from the dried organic layer under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was further purified by flash column chromatography

Sources & evidence

ORD record
ord-5223f72df78c44ba86fd907b12e3069a
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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