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

HRID 244414Notes

Reaction equation

HRID 244414 reaction equation
[CH3:1][C:2]1[C:3](=[O:30])[NH:4][CH:5]=[C:6]([C:8]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:18]=[CH:17]3)([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:7]=1.[H-].[Na+].I[CH3:34]>CN(C=O)C.O>[CH3:34][N:4]1[CH:5]=[C:6]([C:8]([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:13])[C:9]([F:10])([F:11])[F:12])[CH:7]=[C:2]([CH3:1])[C:3]1=[O:30]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594372053-Methyl-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyridin-2-one

Product 1

HCID 594372071,3-Dimethyl-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyridin-2-oneYield 27.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-5-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyridin-2-one (0.184 mmol) in 1 mL DMF was added NaH (0.221 mmol; 60% suspension in oil) in several portions. After 1 hour, iodomethane (0.20 mmol) was added. After 1 hour, the mixture was diluted with water and the solid was collected by filtration, washed with water and dried. The residue was purified with flash silica gel chromatography using 25% hexanes in ethyl acetate. The product-rich fractions were concentrated in vacuo to provide the title compound (0.051 mmol), m.p.>200° C.

Workup

  1. waitAfter 1 hour
  2. filtrationthe solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe residue was purified with flash silica gel chromatography
  6. concentrationThe product-rich fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-16ab3c88a6e3489db9d38079d8b68530
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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