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Tetrabutylammonium Fluoride → tert-butyl 5-ethynyl-3-(pyridin-4-yl)-1H-indazole-1-carboxylate

HRID 1465692
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1465692
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[C:17][Si](C(C)C)(C(C)C)C(C)C)[CH:14]=3)[N:9]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:8]=2)=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:8]=[C:7]2[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)#[CH:17]
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Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67517348tert-butyl 3-(pyridin-4-yl)-5-((triisopropylsilyl)ethynyl)-1H-indazole-1-carboxylate

Produkt 1

HCID 86695574tert-butyl 5-ethynyl-3-(pyridin-4-yl)-1H-indazole-1-carboxylateAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 3-(pyridin-4-yl)-5-((triisopropylsilyl)ethynyl)-1H-indazole-1-carboxylate (3.10 g, 6.5 mmol) in THF (100 ml) was added 1M TBAF in THF (7.2 ml, 7.2 mmol). The reaction was stirred for 3 h at room temperature. Upon completion, the reaction mixture was quenched with the addition of saturated aqueous NH4Cl (50 ml) and extracted with Et2O (3×100 ml). The combined organic extracts were washed with saturated aqueous NaCl (100 ml) and dried with anhydrous Na2SO4. The organic phase was concentrated under reduced pressure and column purified (20-80% EtAOc/Hexane) to give the desired product of tert-butyl 5-ethynyl-3-(pyridin-4-yl)-1H-indazole-1-carboxylate (0.77 g) and the de-Boc product of 5-ethynyl-3-(pyridin-4-yl)-1H-indazole (0.40 g).

Aufarbeitung

  1. customUpon completion, the reaction mixture was quenched with the addition of saturated aqueous NH4Cl (50 ml)
  2. extractionextracted with Et2O (3×100 ml)
  3. washThe combined organic extracts were washed with saturated aqueous NaCl (100 ml)
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationThe organic phase was concentrated under reduced pressure and column
  6. custompurified (20-80% EtAOc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8d3c662ad0334b3b9d26e22c92a90df6
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999966B2

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