5-Fluoro-3-methyl-1H-indole-2-carboxylic acid → 5-Fluoro-3-methyl-1H-indole

HRID 2219449Notes

Reaction equation

HRID 2219449 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](C(O)=O)=[C:5]2[CH3:14]>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:14]

Participants

4

Reactant 1

HCID 11329675-Fluoro-3-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 223515035-Fluoro-3-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

5-fluoro-3-methyl-1H-indole-2-carboxylic acid (8.49 g, 43.9 mmol) and copper metal (0.35 g, 5.5 mmol) in distilled quinoline (22 mL) was heated to reflux for 3 hours. The copper powder was filtered off and the filtrate was brought to pH 3 at 0° C. with a 6N aqueous solution of hydrochloric acid. The solution was extracted with ether (200 mL) and the organics washed with saturated sodium chloride (200 mL), dried over magnesium sulfate and concentrated in vacuo to give 5-fluoro-3-methyl-1H-indole as a brown solid. MS (ES) m/z 150.0.

Workup

  1. temperatureto reflux for 3 hours
  2. filtrationThe copper powder was filtered off
  3. customwas brought to pH 3 at 0° C. with a 6N aqueous solution of hydrochloric acid
  4. extractionThe solution was extracted with ether (200 mL)
  5. washthe organics washed with saturated sodium chloride (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-676671e5827a43928c8f890f4e435d94
Source dataset
uspto-grants-2008_08
Patent number
US07414052B2

Reaction notes

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