Isobutyl iodide → 4-Methyl-6-(3-methylbutyl)-2-(2,5-dimethylpyrrol-1-yl)pyridine

HRID 1740982Notes

Reaction equation

HRID 1740982 reaction equation
C1([Li])C=CC=CC=1.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])[CH:10]=1.I[CH2:24][CH:25]([CH3:27])[CH3:26].[I-]>C(OCC)C.C1CCCCC1.C(OCC)C>[CH3:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:24][CH:25]([CH3:27])[CH3:26])[N:12]=[C:11]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])[CH:10]=1

Participants

7

Reactant 4

HCID 10556Isobutyl iodideHCID 30165Iodide IonHCID 224907362-(2,5-Dimethyl-1H-pyrrol-1-yl)-4,6-dimethylpyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 218344034-Methyl-6-(3-methylbutyl)-2-(2,5-dimethylpyrrol-1-yl)pyridineYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
-10 °C

Procedure

A solution prepared by the addition of 1.58 mL (2.85 mmol) of 1.8 M phenyllithium in 70:30 cyclohexane/diethyl ether to 4.0 mL of diethyl ether was stirred at -10° C. 4,6-Dimethyl-2-(2,5-dimethylpyrrol-1-yl)pyridine (500 mg, 2.5 mmol) was added as a solution in 1.7 mL of diethyl ether and the mixture was stirred 1h at -5 to -10° C. The red solution was then cooled to -45° C. and 0.354 mL (566 mg, 3.08 mmol) of 1-iodo-2-methylpropane was added in one portion. The reaction was warmed slowly to 10° C., stirring a total 2 h after addition of the iodide. The reaction was then quenched with 10 mL of saturated aqueous ammonium chloride and extracted with 30 mL of ethyl acetate. The organic phase was washed with 10 mL of saturated aqueous sodium chloride, dried over sodium sulfate and concentrated to give a yellow oil. Purification by flash column chromatography on silica gel, eluting with dichloromethane/hexane yielded 330 mg (52% yield) of 4-methyl-6-(3-methylbutyl)-2-(2,5-dimethylpyrrol-1-yl)pyridine as a yellow oil.

Workup

  1. temperatureThe red solution was then cooled to -45° C.
  2. temperatureThe reaction was warmed slowly to 10° C.
  3. stirringstirring a total 2 h
  4. customThe reaction was then quenched with 10 mL of saturated aqueous ammonium chloride
  5. extractionextracted with 30 mL of ethyl acetate
  6. washThe organic phase was washed with 10 mL of saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. customPurification by flash column chromatography on silica gel
  11. washeluting with dichloromethane/hexane

Sources & evidence

ORD record
ord-eea33b4f28404f5f9e0c5ae3606347c0
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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