Ethyl Acetate → HCID 22037958, compound

HRID 1790435Notes

Reaction equation

HRID 1790435 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=4)C(=O)C3=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:22]3[CH:17]=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[CH2:10][CH2:9]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 220380051-[1-(4-Fluorophenethyl)-piperidin-4-yl]-2,3-dioxo-6-bromoindoline

Product 1

HCID 22037958HCID 22037958, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, a 1 M solution (69 ml) of a borane/tetrahydrofuran complex in tetrahydrofuran was added dropwise into a solution of 1-[1-(4-fluorophenethyl)-piperidin-4-yl]-2,3-dioxo-6-bromoindoline (7.4 g) in tetrahydrofuran (150 ml) followed by stirring at room temperature overnight and heating under reflux for 3 hr. Into the reaction solution was carefully added dropwise a saturated aqueous solution of sodium bicarbonate. Then ethyl acetate was added to the resultant mixture and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then diluted with pyridine (50 ml) and stirred at room temperature for 4 hr. Next, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto and the layers were separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (3.9 g) as a yellow oil (yield: 57%).

Workup

  1. temperatureheating
  2. temperatureunder reflux for 3 hr
  3. customthe organic layer was separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was then diluted with pyridine (50 ml)
  8. stirringstirred at room temperature for 4 hr
  9. additionNext, a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added
  10. customthe layers were separated
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-1e67596720d74f23a89845765389e7b4
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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