Benzene → Methyl 4-fluoro-1H-indole-7-carboxylate

HRID 992353Notes

Reaction equation

HRID 992353 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH:14]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 115792174-fluoro-1H-indole-7-carboxylic Acid

Product 1

HCID 22473012Methyl 4-fluoro-1H-indole-7-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-fluoro-7-carboxyindole in a mixture of MeOH (18 ml)/PhH (62 ml) was added (trimethylsilyl)diazomethane (8.8 ml, 17.6 mmol, 2 M in hexane). The resulting mixture was stirred at room temperature for 30 min., quenched with excess acetic acid and evaporated in vacuo. The crude oily material was purified by flash chromatography using a gradient elution (Hexane to 10% EtOAc/Hexane) to afford methyl (4-fluoro)indole-7-carboxylate as a white solid (1.04 g, 83% two steps)

Workup

  1. customquenched with excess acetic acid
  2. customevaporated in vacuo
  3. customThe crude oily material was purified by flash chromatography
  4. washa gradient elution (Hexane to 10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-2f8c875a55f645879ba671a1cd6d23d5
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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