Ethanol → ethyl 1-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylate

HRID 1012264Notes

Reaction equation

HRID 1012264 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:20]#N)=[CH:18][CH:19]=[C:14]2[C:13]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](Cl)(=[O:30])[CH3:29].C([OH:34])C>>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:20]([O:30][CH2:28][CH3:29])=[O:34])=[CH:18][CH:19]=[C:14]2[C:13]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 231526791-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carbonitrile

Product 1

HCID 23152849ethyl 1-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylateYield 70%

Procedure

To a solution of 1-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carbonitrile (1.44 g, 4.00 mmol) in ethanol (30 ml) was added acetyl chloride (8.5 ml, 120 mmol) under ice-cooling, and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and water was added. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give ethyl 1-(2-benzyloxyethyl)-3-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylate (1.14 g, yield 70%).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hr
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additionwater was added
  7. extractionThe mixture was extracted with ethyl acetate
  8. washthe organic layer was washed successively with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1b4a5d50e5bb44bca031be7a06199136
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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