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

HRID 876466Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-900b1a954caa4ba5817f0e686b875513
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987251B2

Reaction notes

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