Tetrabutylammonium Fluoride → 4-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

HRID 1696201Notes

Reaction equation

HRID 1696201 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=[CH:11][C:3]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 534382514-Chloro-5-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridineYield 95.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution 4-chloro-5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.04 g) in tetrahydrofuran (4.77 mL) was added dropwise tetra-n-butylammonium fluoride (0.372 mL, 1.0M in tetrahydrofuran) at ambient temperature. After stirred for 1 hour, the mixture was poured into brine (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layeres were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/EtOAc=1/1) to give 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (520 mg) as a colorless solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic layeres were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, n-hexane/EtOAc=1/1)

Sources & evidence

ORD record
ord-563bd0b13e2240b49b8af68653b75d23
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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