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

HRID 79593Notes

Reaction equation

HRID 79593 reaction equation
[Br: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>[Br: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 497589465-Bromo-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534129385-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridineYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyri dine (12.60 g, 33.9 mmol) was placed in THF (200 mL) at 0° C. TBAF (33.9 mL, 1M THF solution) was then added, and the reaction was then stirred for 1 hour at 0° C. The reaction was quenched with NaHCO3 (aq.) and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:5 DCM:MeOH) to give 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (6.8 g, 93.2% yield).

Workup

  1. customThe reaction was quenched with NaHCO3 (aq.)
  2. extractionextracted into DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue that
  7. customwas purified by column chromatography (500:5 DCM:MeOH)

Sources & evidence

ORD record
ord-53ad33b44a4b405485ecde24de619211
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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