Methyl iodide → HCID 66849144, compound

HRID 2205755Notes

Reaction equation

HRID 2205755 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-10cc273f20c547d2a5c4da1942758515
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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