Tetrabutylammonium Fluoride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 2108739Notes

Reaction equation

HRID 2108739 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][N:26]([Si](C(C)C)(C(C)C)C(C)C)[C:23]2=[N:24][CH:25]=1>C1COCC1>[F:19][C:20]1[CH:21]=[C:22]2[CH:28]=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 242292265-Fluoro-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylamonium fluoride, 1M in THF (2 mL), was added to a stirred solution of 5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1 g, 3.94 mmol) in THF (10 mL) at room temperature and stirred for 15 min. The solvent was evaporated and the crude product was purified by Biotage HPFC system (40-75% EtOAc/Hexane) to afford 5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (0.45 g, 84); Mass Spec.; MS 137 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.75(s, 1H), 8.17(t,1H), 7.81(dd,1H), 7.55(t,1H), 6.44(dd,1H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by Biotage HPFC system (40-75% EtOAc/Hexane)

Sources & evidence

ORD record
ord-fb6d70854c7547e5a9b8229033fd6e68
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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