Benzyl Bromide → Methyl 1-benzyl-3-methyl-pyrrole-2-carboxylate

HRID 642555Notes

Reaction equation

HRID 642555 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][C:9]=1[CH3:10])=[O:4].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 24271768methyl 3-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 68428595Methyl 1-benzyl-3-methyl-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice/water-bath cooled solution of 3-methyl-1H-pyrrole-2-carboxylic acid methyl ester (1.196 g, prepared according to the literature: W. G. Terry, G. W. Kenner, and G. Kornis J. Chem. Soc. 1965, 4389-4393) and benzyl bromide (1.15 mL) in N,N-dimethylformamide (17 mL) was carefully added NaH (413 mg, 60% purity in mineral oil) under nitrogen. The mixture was stirred in the ice bath for 25 min and then quenched saturated ammonium chloride solution (5 mL). It was extracted with EtOAc, and the organic phase was washed with water and saturated NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated. The crude residue was column-purified to give the title compound (1.536 g) as white solid. 1H NMR (200 MHz, CDCl3) δ=7.32-6.98 (m, 5H), 6.75 (d, 1H, J=2.5 Hz), 6.02 (d, 1H, J=2.5 Hz), 5.48 (s, 2H), 3.75 (s, 3H), 2.33 (s, 3H).

Workup

  1. customprepared
  2. extractionIt was extracted with EtOAc
  3. washthe organic phase was washed with water and saturated NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was column-purified

Sources & evidence

ORD record
ord-ea4ee911fb5b4ce88a096ae81a2bf7dc
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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