Tetrabutylammonium Fluoride → 5-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine

HRID 1034653Notes

Reaction equation

HRID 1034653 reaction equation
[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 602052735-Chloro-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridineYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 9.18 mmol) was placed in THF (15 mL) at 0° C. TBAF (10.094 mL, 10.094 mmol) was added dropwise and stirred for 30 minutes. The reaction was then quenched with saturated aqueous NaHCO3 and extracted into DCM. The combined organic fractions were dried, filtered, and concentrated to give the crude product that was purified by column chromatography (500:6 DCM:MeOH) to give 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.4 g, 89% yield).

Workup

  1. customThe reaction was then quenched with saturated aqueous NaHCO3
  2. extractionextracted into DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product that
  7. customwas purified by column chromatography (500:6 DCM:MeOH)

Sources & evidence

ORD record
ord-cdd08eb2a44e48aca05dc000807508df
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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