Methyl iodide → HCID 66849144, compound

HRID 406450Notes

Reaction equation

HRID 406450 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[H-].[Na+].[CH3:26]I>C1COCC1>[CH3:26][O:21][C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:1])([F:22])[F:23])=[N:4][N:5]=3)[CH:8]=2)=[CH:13][CH:14]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58119000HCID 58119000, compound

Product 1

HCID 66849144HCID 66849144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 10-mL cone-shaped flask equipped with a magnetic stir bar 2-(4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl)propan-2-ol (28 mg) was dissolved in dry THF (1 mL) and NaH (60% suspension in mineral oil, 20 eq.) and MeI (50 eq.) were added. The reaction mixture was stirred overnight at room temperature. Extracted with water and EtOAc, organic layer dried over MgSO4, concentrated, and purified by chromatography (3% MeOH in methylene chloride). The desired 6-(4-(2-methoxypropan-2-yl)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine was isolated.

Workup

  1. extractionExtracted with water and EtOAc, organic layer
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by chromatography (3% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-fcf78a16224c4a3facacdbb623456bc1
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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