Water → (S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]-N-methyl-4-(1-methyl-1H-pyrazol-4-yl)pyridine-2-amine

HRID 1187734Notes

Reaction equation

HRID 1187734 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[C:4]([C:18]2[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=2)[CH:3]=1.[H-].[Na+].[CH3:26]I.O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH3:10])[CH3:26])[CH:5]=[C:4]([C:18]2[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide3×HCID 24758Sodium hydride3×HCID 86659376HCID 86659376, compound

Product 1

HCID 86659405(S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]-N-methyl-4-(1-methyl-1H-pyrazol-4-yl)pyridine-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

92 mg of (S)-6-chloro-N-[1-(4-fluorophenyl)ethyl]-4-(1-methyl-1H-pyrazol-4-yl)pyridine-2-amine was dissolved in 1.5 ml of tetrahydrofuran, and 17 mg of 60% sodium hydride was added thereto, and the mixture was stirred at room temperature for 10 minutes. 26 μl of methyl iodide was added thereto, and the reaction solution was subjected to microwave irradiation at 100° C. for 5 minutes. 8 mg of 60% sodium hydride and 26 μl of methyl iodide were added to the reaction solution, and the reaction solution was stirred at 130° C. for 10 minutes, and furthermore 17 mg of 60% sodium hydride and 26 μl of methyl iodide were added, and the mixture was stirred at 130° C. for 10 minutes. The reaction solution was added with water and subjected to extraction with ethyl acetate. The organic layer was washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 62 mg of the objective compound as pale yellow oil.

Workup

  1. customirradiation at 100° C. for 5 minutes
  2. stirringthe reaction solution was stirred at 130° C. for 10 minutes
  3. stirringthe mixture was stirred at 130° C. for 10 minutes
  4. extractionsubjected to extraction with ethyl acetate
  5. washThe organic layer was washed in turn with water and brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7df9b3aaa93a474c9856ba0ef3c43953
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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