Water → HCID 12390499, compound

HRID 339720Notes

Reaction equation

HRID 339720 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].I[CH3:19].[H-].[Na+].O>C1COCC1>[CH3:19][N:3]1[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12258777Ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 12390499HCID 12390499, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate (3 g, 13 mmol) in THF (50 ml) was added iodomethane (4 ml, 65 mmol) and sodium hydride (630 mg, 60% in mineral oil, 15.6 mmol) at 0° C. After warming the reaction mixture to room temperature, it was stirred for 1 day. Water (20 ml) was added and extracted organic layer with diethyl ether. With normal-phase preparative LC, purification preceded to gave title compound (3 g, 94%) as yellow solid.

Workup

  1. extractionextracted organic layer with diethyl ether
  2. customWith normal-phase preparative LC, purification

Sources & evidence

ORD record
ord-01131ca612b34ffd9d66fd2aec2f178a
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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