Methyl iodide → HCID 66849144, compound

HRID 1846962Notes

Reaction equation

HRID 1846962 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-cd3f9162b1fc421ea4d6b44cc4828598
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

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