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

HRID 1841696Notes

Reaction equation

HRID 1841696 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].[K].C(=O)([O-])[O-].I[CH2:19][CH:20]([CH3:23])[CH2:21][CH3:22]>CC(C)=O>[CH3:19][CH:20]([CH2:21][CH3:22])[CH2:23][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

6

Reactant 4

HCID 19660Carbonate IonHCID 1414791-Iodo-2-methylbutaneHCID 261887Methyl 4-nitro-1h-pyrrole-2-carboxylateHCID 5462222Potassium

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 vacuo, 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) δ 8.30 (d, 1H, J=2.0 Hz), 7.33 (d, 1H, J=1.9 Hz), 4.15 (d, 2H, J=7.4 Hz), 3.77 (s, 3H), 2.03 (m, 1H, J=3.1 Hz), 0.80 (d, 6H, J=6.7 Hz); 13C NMR (DMSO-d6) δ 160.30, 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 vacuo
  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-835d3c7625384a36814879dc04762286
Source dataset
uspto-grants-2004_01
Patent number
US06683189B1

Reaction notes

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