ethyl 5-fluoro-1H-indole-2-carboxylate → 934969-76-3

HRID 1038441Notes

Reaction equation

HRID 1038441 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](OCC)=[O:12])=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[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

Participants

4

Reactant 2

HCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 69408498934969-76-3Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 5-fluoro-1H-indole-2-carboxylate 45 (3.1 g, 14.96 mmol) in THF at 0° C. was added lithium aluminum hydride solution (1 M, in THF 0.625 g, 16.44 mmol) dropwise and the reaction mixture was stirred for 3.5 hours at 0° C. The reaction mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed with THF. Reaction mixture was dried (anhydrous Na2SO4) and evaporation of the solvent gave 2.21 g (90% yield) of the crude (5-fluoro-1H-indol-2-yl)methanol 46 which was used directly in the next step.

Workup

  1. customThe reaction mixture was quenched with H2O, 15% NaOH, and H2O before it
  2. filtrationwas filtered
  3. washrinsed with THF
  4. customReaction mixture
  5. customwas dried
  6. custom(anhydrous Na2SO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-045e87634bb6492aa095e154105d9035
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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