Water → methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylate

HRID 505821Notes

Reaction equation

HRID 505821 reaction equation
[Cl:1][C:2]1[NH:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([N:3]1[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]1[Cl:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66974443methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate

Product 1

HCID 68468834methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution (7 M) of methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate in DMF at 0° C. was treated with NaH (1.2 eq., 60% dispersion in mineral oil), and the suspension was stirred at RT for 30 min then it was treated with benzyl bromide (1.2 eq.). The reaction mixture was stirred at RT for 90 min then poured into water and extracted with AcOEt. The combined organic phase was washed with water and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:8 AcOEt/petroleum ether) to afford the title compound (71%) as a solid.

Workup

  1. stirringThe reaction mixture was stirred at RT for 90 min
  2. extractionextracted with AcOEt
  3. washThe combined organic phase was washed with water
  4. customdried
  5. customEvaporation of the solvent
  6. customgave a residue that
  7. customwas purified by flash chromatography on silica gel (1:8 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-0b88e83c557848fea88c13f6fb24b3ee
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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