Tetrabutylammonium Fluoride → (E)-3-(2-(4-methylthiazol-5-yl)vinyl)-1H-indazole-6-carbaldehyde

HRID 1615315Notes

Reaction equation

HRID 1615315 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1/[CH:7]=[CH:8]/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=2)[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86651974(E)-3-(2-(4-methylthiazol-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 86651975(E)-3-(2-(4-methylthiazol-5-yl)vinyl)-1H-indazole-6-carbaldehydeYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-3-(2-(4-methylthiazol-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazole-6-carbaldehyde (30 mg, 0.075 mmol) and tetrabutyl-ammonium fluoride (1.0 M in THF, 0.37 mL, 0.37 mmol) in anh. THF (10 mL) was refluxed under Ar for 1 d. The reaction mixture was then concentrated under reduced pressure and purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound (15 mg, 74%) as a tan solid (7.0 mg, 21%). MS ESI 270.0 [M+H]+, calcd for [C14H11N3OS+H]+ 270.3.

Workup

  1. temperaturewas refluxed under Ar for 1 d
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. custompurified by prepTLC (SiO2 10% MeOH/DCM)

Sources & evidence

ORD record
ord-11b14981c697414b87ffa7cfbd314c1e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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