934969-76-3 → 5-Fluoro-1H-indole-2-carbaldehyde

HRID 537874Notes

Reaction equation

HRID 537874 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]=[O:12])=[CH:5]2

Participants

5

Reactant 2

HCID 69408498934969-76-3HCID 178418287HCID 178418287, compound

Product 1

HCID 189681295-Fluoro-1H-indole-2-carbaldehydeYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of crude (5-fluoro-1H-indol-2-yl)methanol 46 (1.55 g, 9.39 mmol) in anhydrous CH2Cl2 (50 mL) at cold-bath temperature (0° C.) was added portionwise pyridinium chlorochromate (PCC) (2.22 g, 10.29 mmol). Reaction was stirred at ambient temperature for 4 hours. Reaction was diluted with CH2Cl2 and filtered through a pad of celite and washed with CH2Cl2. After evaporation of solvent, crude product was silica-column chromatographed (Biotage) using Acetone:Hexane as an eluent to yield 5-fluoro-1H-indole-2-carbaldehyde 47 (0.627 g, 41% yield).

Workup

  1. customReaction
  2. customReaction
  3. filtrationfiltered through a pad of celite
  4. washwashed with CH2Cl2
  5. customAfter evaporation of solvent, crude product
  6. customchromatographed (Biotage)

Sources & evidence

ORD record
ord-9ac272ee83fe452b88b0c0bdafdec5de
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Reaction notes

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