Ethyl bromoacetate → Ethyl 5-bromo-6-fluoro-1H-indole-1-acetate

HRID 1945308Notes

Reaction equation

HRID 1945308 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[F:13])[NH:9][CH:8]=[CH:7]2.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[C:12]([F:13])[CH:11]=2)[CH:7]=[CH:8]1)[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 116871455-bromo-6-fluoro-1H-indole

Product 1

HCID 86640506Ethyl 5-bromo-6-fluoro-1H-indole-1-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (81 mg, 3.21 mmol) was added to a 0° C. solution of 5-bromo-6-fluoro-1H-indole (0.343 g, 1.60 mmol) in THF (16 mL). The reaction mixture was stirred at 0° C. for 15 min, then ethyl bromoacetate (0.535 mL, 4.81 mmol) was added. The reaction was stirred at rt for 1 h, then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude product was used in the next step without further purification.

Workup

  1. stirringThe reaction was stirred at rt for 1 h
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-6cdfe8153d384caf93eb044a18277248
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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