Dimethylformamide → 4-fluoro-1H-indole-7-carbaldehyde

HRID 992354Notes

Reaction equation

HRID 992354 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8](Br)=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Li]CCCC.CN([CH:20]=[O:21])C>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH:20]=[O:21])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 43429567-bromo-4-fluoro-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 185197774-fluoro-1H-indole-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-fluoro-7-bromoindole (1.0 g, 4.7 mmol) in THF (5 mL) at −78° C. was added n-BuLi (5.6 mL, 2.5M in hexanes) dropwise. The mixture was stirred for 15 min at −78° C., was allowed to warm to 5° C. for 30 min and was then re-cooled to −78° C. DMF (1.8 mL) was then added and the mixture was allowed to warm to room temperature slowly. The reaction was quenched with water and was extracted with ether. The organic phase was dried over MgSO4, filtered and concentrated to afford 4-fluoroindole-7-carboxaldehyde.

Workup

  1. temperatureto warm to 5° C. for 30 min
  2. temperaturewas then re-cooled to −78° C
  3. temperatureto warm to room temperature slowly
  4. customThe reaction was quenched with water
  5. extractionwas extracted with ether
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f3e3b5c7853548f0ab5f0673874e59f3
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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