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

HRID 250604Notes

Reaction equation

HRID 250604 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11]([Si](C(C)C)(C(C)C)C(C)C)[C:8]2=[N:9][CH:10]=1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 666792441-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester

Product 1

HCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (531, 0.950 g, 2.9 mmol) in tetrahydrofuran (20.0 mL) was added tetrabutyl-ammonium fluoride, trihydrate (1.20 g, 3.8 mmol). The reaction was stirred at room temperature for 10 minutes. The reaction was concentrated and purified with silica gel column chromatography eluting with 4% methanol in methylene chloride to give the compound as a white solid (532, 300 mg, 60%). MS (ESI) [M+H+]+=177.2.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified with silica gel column chromatography
  3. washeluting with 4% methanol in methylene chloride

Sources & evidence

ORD record
ord-be303498cdeb4158b4dffb0016e4a4db
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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