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

HRID 490502Notes

Reaction equation

HRID 490502 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

Conditions

Temperature
130 °C

Procedure

A mixture of 3.80 g of 5-fluoro-3-trimethylsilanylethynylpyrid-2-ylamine and 3.40 g of potassium tert-butoxide in 100 cm3 of 1-methylpyrrolidin-2-one is maintained in the region of 130° C. for about 4 hours. After cooling to a temperature in the region of 20° C., the mixture is poured into 1000 cm3 of saturated aqueous sodium chloride solution and extracted with 5 times 250 cm3 of diethyl oxide. The organic phases are combined, washed with 5 times 100 cm3 of 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. temperatureAfter cooling to a temperature in the region of 20° C.
  2. extractionextracted with 5 times 250 cm3 of diethyl oxide
  3. washwashed with 5 times 100 cm3 of 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-29ab2fe2330b432596a066896baf0543
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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