Tetrabutylammonium Fluoride → HCID 118208787, compound

HRID 595266Notes

Reaction equation

HRID 595266 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][N:29]1[CH:33]=[C:32]([C:34]2[N:39]=[C:38]([NH:40][C:41]3[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[CH:43][N:42]=3)[CH:37]=[C:36]([CH3:51])[CH:35]=2)[CH:31]=[N:30]1)(C(C)(C)C)(C)C>ClCCl>[CH3:51][C:36]1[CH:37]=[C:38]([NH:40][C:41]2[CH:46]=[C:45]([C:47]([F:50])([F:48])[F:49])[CH:44]=[CH:43][N:42]=2)[N:39]=[C:34]([C:32]2[CH:31]=[N:30][N:29]([CH2:28][CH2:27][OH:26])[CH:33]=2)[CH:35]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734581HCID 131734581, compound

Product 1

HCID 118208787HCID 118208787, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TBAF (1.0 M, 0.11 mL, 0.11 mmol) was added to a solution of 6-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazol-4-yl]-4-methyl-N-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine in dichloromethane (2 mL). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 10% MeOH/dichloromethane) to afford 2-[4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1H-pyrazol-1-yl]ethanol. MS ESI C17H16F3N5O [M+H]+ 364. found 364.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (0 to 10% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-a795be7277584661bb68a7fa89636370
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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