Sodium Hydroxide → HCID 22561919, compound

HRID 1839588Notes

Reaction equation

HRID 1839588 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[C:16]([F:18])[CH:17]=1.[OH-].[Na+]>C1COCC1.[Pd]>[F:11][C:12]1[CH:13]=[C:14]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[CH:5][NH:6]3)[CH:15]=[C:16]([F:18])[CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 6764944-BromoindoleHCID 2734338(3,5-Difluorophenyl)boronic acid

Product 1

HCID 22561919HCID 22561919, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-bromoindole (12.42 g, 63.3 mmol), and 3,5-difluorophenylboronic acid (10.0 g, 63.3 mmol) in THF (108 mL) were added Palladium catalyst Pd(PPh3)4 (2.2 g, 1.9 mmol) and the freshly prepared sodium hydroxide solution (7.6 g, 190 mmol in 89 mL water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 85° C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, filtered through celite, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by a silica gel column to provide 4-(3,5-difluoro-phenyl)-1H-indole.

Workup

  1. customThe system was degassed
  2. additioncharged with nitrogen
  3. customthe completion of the coupling reaction
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered through celite
  6. additiondiluted with ethyl acetate
  7. customseparated from water layer
  8. washThe ethyl acetate solution was washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe crude product was purified by a silica gel column

Sources & evidence

ORD record
ord-81f3360ce98c4fb9a1db75668febd53c
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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