Tetrabutylammonium Fluoride → HCID 59577355, Verbindung

HRID 1526042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526042
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:38]=[C:37]([N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)[CH:36]=[CH:35][C:13]=1[C:14]([NH:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=3)[CH:24]=2)[NH:19][N:18]=1)=[O:15])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:33][C:31]1[CH:32]=[C:27]([CH:28]=[C:29]([F:34])[CH:30]=1)[CH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][N:18]=[C:17]2[NH:16][C:14](=[O:15])[C:13]1[CH:35]=[CH:36][C:37]([N:39]2[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]2)=[CH:38][C:12]=1[NH:11][CH2:10][CH2:9][OH:8]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 68671892HCID 68671892, Verbindung

Produkt 1

HCID 59577355HCID 59577355, VerbindungAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide (126 mg, 0.2 mmol) was dissolved in dry THF (3 mL) and 1M TBAF in THF (0.24 mL) was added at 0° C. The resulting solution was stirred overnight at room temperature. Reaction was quenched with water and extracted with ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and evaporated to dryness. Residue was purified by column chromatography over silica gel (DCM/EtOH/NH3 5N in MeOH=85/15/1) affording 83 mg of title compound.

Aufarbeitung

  1. customReaction
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialCollected organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customResidue was purified by column chromatography over silica gel (DCM/EtOH/NH3 5N in MeOH=85/15/1)

Quellen und Nachweise

ORD-Eintrag
ord-ef26a94ccc864f1794dc35c1987d2581
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085558B2

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