Iodoethane → 1H-Pyrrolo[2,3-b]pyridine, 1-ethyl-

HRID 2394371Notes

Reaction equation

HRID 2394371 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[CH2:12](I)[CH3:13]>CC(C)=O>[CH2:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1)[CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium Hydroxide

Product 1

HCID 118191871H-Pyrrolo[2,3-b]pyridine, 1-ethyl-Yield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 grams (0.0846 moles) of 7-azaindole (Aldrich (trademark)) were dissolved in 200 mL of reagent grade acetone at room temperature and treated with 10 grams (0.178 moles) of powdered KOH. After~2-3 minutes, 67 mL (0.846 moles) of ethyl iodide was added over a period of 5-10 minutes and the reaction mixture was stirred at room temperature for 30-40 minutes. Thin layer chromatography (TLC) using 95% methylene chloride/5% ethyl acetate showed complete consumption of the starting material and formation of a single less polar product. The reaction mixture was concentrated in vacuo and the residue was partitioned between water and methylene chloride (350 mL). The organic layer was separated and washed with water and brine and dried (sodium sulfate). Concentration of the organic extract in vacuo gave a yellow-brown oil which was purified on a silica gel column eluting with methylene chloride/ethyl acetate (95%/5%). A total of 11.15 grams (90%) of pure final product (light yellow oil) was obtained.

Workup

  1. custom95% methylene chloride/5% ethyl acetate showed complete consumption of the starting material and formation of a single less polar product
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and methylene chloride (350 mL)
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. extractionConcentration of the organic extract in vacuo
  8. customgave a yellow-brown oil which
  9. customwas purified on a silica gel column
  10. washeluting with methylene chloride/ethyl acetate (95%/5%)

Sources & evidence

ORD record
ord-138c29916ac64c69a849671c5265f5be
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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