Sodium hydride → 6-fluoro-1H-pyrrolo(3,2-b)pyridine

HRID 2409037Notes

Reaction equation

HRID 2409037 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]([C:8]#[C:9][Si](C)(C)C)=[N:6][CH:7]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[NH:14][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 866898515-Fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine

Product 1

HCID 534130836-fluoro-1H-pyrrolo(3,2-b)pyridineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-fluoro-2-((trimethylsilyl)ethynyl)pyridin-3-amine (2.22 g, 10.7 mmol) in DMF (30 mL) at 0° C. under nitrogen was added NaH (60% in mineral oil, 1.025 g, 42.7 mmol) in several portions. After stirring at RT for 2 h, the reaction mixture was poured into ice-cold water and extracted with EtOAc. The extract was dried (MgSO4), filtered, and concentrated under reduced pressure to afford 1.46 g (100%) of 6-fluoro-1H-pyrrolo[3,2-b]pyridine as a brown solid. MS (ESI): m/z=137.2 [M+1]+.

Workup

  1. additionthe reaction mixture was poured into ice-cold water
  2. extractionextracted with EtOAc
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eee115398dd84102b74d35a0db7467ec
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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