Tetrabutylammonium Fluoride → HCID 57691784, compound

HRID 422340Notes

Reaction equation

HRID 422340 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C[Si](C)(C)[C:21]#[C:22][CH2:23][CH2:24][N:25]1[CH:33]=[C:32]2[C:27]([CH:28]=[CH:29][CH:30]=[CH:31]2)=[N:26]1.C[Si](C)(C)C#CCCN1C2C(=CC=CC=2)C=N1.C(N1C2C(=CC=CC=2)C=N1)CC#C>C1COCC1.O>[CH2:24]([N:25]1[CH:33]=[C:32]2[C:27]([CH:28]=[CH:29][CH:30]=[CH:31]2)=[N:26]1)[CH2:23][C:22]#[CH:21]

Participants

7

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 57691801HCID 57691801, compoundHCID 63655048HCID 63655048, compoundHCID 66598009HCID 66598009, compound

Product 1

HCID 57691784HCID 57691784, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.24 mL, 1.24 mmol) was added to a solution of 2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole and 1-(4-trimethylsilanyl-but-3-ynyl)-1H-indazole (250 mg, 1.03 mmol) in THF (5 mL) and the reaction mixture was stirred for 2 hours at room temperature. After the addition of water, the solvent was evaporated and the aqueous phase was extracted with DCM. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by bulb-to-bulb distillation (0.2 mbar, 100-120° C.) to yield 160 mg (0.94 mmol, 91%) of 2-(but-3-ynyl)-2H-indazole and 1-(but-3-ynyl)-1H-indazole.

Workup

  1. customthe solvent was evaporated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe crude residue was purified by bulb-to-bulb distillation (0.2 mbar, 100-120° C.)

Sources & evidence

ORD record
ord-e28ec161ac9f45eba34e12f1ee1a9b05
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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