Tetrabutylammonium Fluoride → 90929-76-3

HRID 1948623Notes

Reaction equation

HRID 1948623 reaction equation
C([Si](CC)(CC)[C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]=1[CH2:13][CH2:14][OH:15])C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[NH:12]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]([CH2:13][CH2:14][OH:15])=[CH:4]1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 153510022-(Triethylsilyl)-1H-pyrrolo[2,3-b]pyridine-3-ethanol

Product 1

HCID 1328535590929-76-3Yield 79%

Procedure

2-(2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (1.00 g, 3.62 mmole) was stirred with TBAF (10.86 ml, 10.86 mmole; 1M solution in THF) for 6 hours at 50° C. and then for 10 hours at RT. The solvent was removed on a rotary evaporator and the residue was purified by column chromatography (DCM/MeOH=9:1, then 1:1). 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (0.46 g, 79%) was formed as a white solid.

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was purified by column chromatography (DCM/MeOH=9:1

Sources & evidence

ORD record
ord-b410c59fdb3445308e1fbfa047f79891
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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