Tetrabutylammonium Fluoride → HCID 15351005, compound

HRID 1948629Notes

Reaction equation

HRID 1948629 reaction equation
C([Si](CC)(CC)[C:4]1[NH:16][C:7]2=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:6]2[C:5]=1[CH2:17][CH2:18][OH:19])C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[F:15][C:12]([F:13])([F:14])[C:10]1[CH:11]=[C:6]2[C:5]([CH2:17][CH2:18][OH:19])=[CH:4][NH:16][C:7]2=[N:8][CH:9]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68841605HCID 68841605, compound

Product 1

HCID 15351005HCID 15351005, compoundYield 94.8%

Procedure

2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (3.8 g, 11.0 mmole) was stirred with TBAF (33.1 ml, 33.1 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. 2-(5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2.4 g, 94.5%) was obtained.

Workup

  1. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-5b9fa11f262f4af482351657936275b5
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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