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

HRID 244413
Notes
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Reaction equation

HRID 244413 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 594373112,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methyl-6-methoxypyridin-3-yl)ethanol

Product 1

HCID 594372053-Methyl-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 3283
Diethyl Ether
Solvent

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

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe volatiles were removed in vacuo
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes