Potassium Carbonate → Methyl N-2-methyl-butyl-4-nitropyrrole-2-carboxylate

HRID 1265493Notes

Reaction equation

HRID 1265493 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH:21]([CH3:24])[CH2:22][CH3:23]>CC(C)=O>[CH3:20][CH:21]([CH2:22][CH3:23])[CH2:24][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1414791-Iodo-2-methylbutaneHCID 261887Methyl 4-nitro-1h-pyrrole-2-carboxylate

Product 1

HCID 23446390Methyl N-2-methyl-butyl-4-nitropyrrole-2-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-nitropyrrole-2-carboxylate (22) (2.7 g, 15.9 mmol), potassium carbonate (6.5 g), and iodo-2-methylbutane (5.2 ml) were dissolved in 100 ml of acetone and refluxed for 10 hours. The reaction mixture was then cooled to room temperature, concentrated in vacua, partitioned between 200 ml of dichloromethane and 200 ml of water and extracted with dichloromethane (2×200 ml). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The resulting yellow oil was purified by flash chromatography to provide the substituted nitro pyrrole 23 (2.5 g, 70% yield). 1H NMR (DMSO-d6) δ8.30 (d, 1 H, J=2.0 Hz), 7.33 (d, 1 H, J=1.9 Hz), 4.15 (d, 2 H, J=7.4 Hz), 3.77 (s. 3H), 2.03 (m, 1 H, J=3.1 Hz), 0.80 (d. 6 H, J=6.7 Hz); 13C NMR (DMSO-d6) δ160.30, 134.79, 129.80, 122.40, 112.76, 105.00, 56.63, 52.41, 29.72, 19.73; FABMS, 226.096 calcd, 226.095 found.

Workup

  1. temperaturerefluxed for 10 hours
  2. concentrationconcentrated in vacua
  3. custompartitioned between 200 ml of dichloromethane and 200 ml of water
  4. extractionextracted with dichloromethane (2×200 ml)
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe resulting yellow oil was purified by flash chromatography

Sources & evidence

ORD record
ord-d59f97753ab347eaaac8cb663981742e
Source dataset
uspto-grants-2003_04
Patent number
US06545162B1

Reaction notes

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