Tetrabutylammonium Fluoride → HCID 86651958, compound

HRID 1615276Notes

Reaction equation

HRID 1615276 reaction equation
[CH:1](/[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)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1](/[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)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22494888HCID 22494888, compound

Product 1

HCID 86651958HCID 86651958, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (E)-3-styryl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (63 mg, 0.166 mmol) in THF (2.0 mL) was treated with TBAF (0.83 mL of a 1M solution in THF) and refluxed overnight. The solvent was removed and the residue re-dissolved into EtOAc. The organics were washed with water (2×), brine (2×) and then dried (MgSO4). The solvent was removed and the residue purified by column chromatography (silica gel, 98:2 CH2Cl2/MeOH) to give the title compound (27 mg, 66%) which was used without further purification. MS ESI 249.0 [M+H]+, calcd for [C16H12N2O+H]+ 249.10.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was removed
  3. dissolutionthe residue re-dissolved into EtOAc
  4. washThe organics were washed with water (2×), brine (2×)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customthe residue purified by column chromatography (silica gel, 98:2 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-746977ac464d40b0a8032c25d78ac4e7
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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