Pyridinium hydrochloride → 3-Methyl-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyridin-2-one

HRID 244413Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)([C:5]1[CH:6]=[N:7][C:8]([O:12]C)=[C:9]([CH3:11])[CH:10]=1)[OH:4].Cl.[NH+]1C=CC=CC=1>CCOCC.O>[CH3:11][C:9]1[C:8](=[O:12])[NH:7][CH:6]=[C:5]([C:3]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[N:18]=[CH:17]3)([OH:4])[C:2]([F:1])([F:30])[F:31])[CH:10]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methyl-6-methoxypyridin-3-yl)ethanol (0.679 mmol) and pyridinium hydrochloride (6.79 mmol) was warmed at 125° C. in a sealed tube for 20 minutes, cooled to room temperature and diluted with ether and water. The organic layer was washed with brine and dried over magnesium sulfate. The volatiles were removed in vacuo and the residue triturated with petroleum ether to provide the title compound.

Workup

temperaturecooled to room temperature
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customThe volatiles were removed in vacuo
customthe residue triturated with petroleum ether

Sources & evidence

ORD record: ord-b1aca0f5cf014c81bbbd742bb6d55d77
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658637B2

Reaction notes

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