Sodium Chloride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 490462Notes

Reaction equation

HRID 490462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][Si](C)(C)C)[C:5]([NH2:8])=[N:6][CH:7]=1.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]2[CH:9]=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 23665647Potassium tert-butoxideHCID 597068495-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridineYield 94.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 3.8 g of 5-fluoro-3-trimethylsilanylethynylpyridin-2-ylamine and 3.4 g of potassium tert-butoxide in 100 ml of 1-methylpyrrolidin-2-one is brought to around 130° C. for approximately 4 hours. After returning to a temperature in the region of 20° C., the mixture is run into 1000 ml of a saturated aqueous sodium chloride solution and extracted with five times 250 ml of diethyl ether. The organic phases are combined, washed with five times 100 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (13 kPa). 2.35 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine are obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customAfter returning to a temperature in the region of 20° C.
  2. extractionextracted with five times 250 ml of diethyl ether
  3. washwashed with five times 100 ml of a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-d374acd764da456aa935bd759d884fb0
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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