4-Bromo-5-fluoro-2-[2-(trimethylsilyl)ethynyl]benzenamine → 5-bromo-6-fluoro-1H-indole

HRID 1945307Notes

Reaction equation

HRID 1945307 reaction equation
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([C:10]#[C:11][Si](C)(C)C)[CH:3]=1>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:7][C:8]=1[F:9])[NH:6][CH:11]=[CH:10]2

Participants

4

Reactant 1

HCID 684948054-Bromo-5-fluoro-2-[2-(trimethylsilyl)ethynyl]benzenamine

Product 1

HCID 116871455-bromo-6-fluoro-1H-indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

CuI (0.932 g, 4.89 mmol) was added to a solution of 4-bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline (0.700 g, 2.45 mmol) in DMF (25 mL). The resulting suspension was heated at 100° C. for 1 h. The reaction mixture was partitioned between 10% aqueous Na2S2O3 and Et2O. The aqueous layer was extracted with Et2O. The combined organic layers were washed with 5 N aqueous NaOH and brine, dried (Na2SO4), filtered, and concentrated. The crude product was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between 10% aqueous Na2S2O3 and Et2O
  2. extractionThe aqueous layer was extracted with Et2O
  3. washThe combined organic layers were washed with 5 N aqueous NaOH and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-5b65f64e3bef4c829e140ff6ee7d89d1
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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