Tetrabutylammonium Fluoride → N-cyclohexyl-5-fluoro-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine
Reaktionsgleichung
[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]3[CH:17]=[CH:16][N:15]([Si](C(C)C)(C(C)C)C(C)C)[C:10]=3[N:11]=[CH:12][C:13]=2[F:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]3[CH:17]=[CH:16][NH:15][C:10]=3[N:11]=[CH:12][C:13]=2[F:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine (50 mL) in tetrahydrofuran (0.7 mL) was added tetra-n-butylammonium fluoride (0.372 mL, 1.0M in tetrahydrofuran) at ambient temperature. The reaction mixture was stirred at ambient temperature for 2 hours, then another 3 equivalent of tetra-n-butylammonium fluoride (0.372 mL) was added. The mixture was heated at 50° C. for 2 hours, at reflux for 6 hours. After cooling to ambient temperature, the mixture was concentrated. The residue was purified by column chromatography (gradient elution, n-hexane to 1:1 n-hexane/EtOAc) to give N-cyclohexyl-5-fluoro-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine (10 mg) as a pale yellow solid.