1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 2-(7-Methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

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Reaktionsgleichung

[Si]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[NH4+].[Cl-].CCOC(C)=O.O>[CH3:28][C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[N:20][N:21]=[C:22]2[CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

8-(tert-butyldimethylsilyloxy)-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline (0.580 g, 1.49 mmol) was suspended in THF (2 mL) and the solution was cooled to 0° C. Tetrabutylammonium fluoride hydrate (0.582 g, 2.23 mmol) was added to the solution and the mixture stirred at 0° C. for 10 minutes, then warmed to ambient temperature and stirred for 4 hours. The mixture was diluted with a saturated aqueous NH4Cl solution and EtOAc. The resulting white solid was isolated by vacuum filtration and was combined with the organic layer which was concentrated. The solid thus obtained was slurried in H2O for 10 minutes and the solids isolated by vacuum filtration and dried to provide the title compound (0.320 g, 78%) as a white solid. MS ESI (+) m/z 277.1 (M+1) detected.

Aufarbeitung

temperaturewarmed to ambient temperature
stirringstirred for 4 hours
customThe resulting white solid was isolated by vacuum filtration
concentrationwas concentrated
customThe solid thus obtained
customthe solids isolated by vacuum filtration
customdried

Quellen und Nachweise

ORD-Eintrag: ord-900b1a954caa4ba5817f0e686b875513
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08987251B2

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