Methyl iodide → 3-(4-Fluorophenyl)-1-methyl-1h-pyrazole

HRID 250752Notes

Reaction equation

HRID 250752 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:16]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH3:16])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178505519HCID 178505519, compound

Product 1

HCID 668688003-(4-Fluorophenyl)-1-methyl-1h-pyrazoleYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 3-(4-fluorophenyl)pyrazole (7.17 g, 44.2 mmol) in dry DMF (60 mL) with NaH (2.2 g, 92.8 mmol) at 0° C. for 15 min. Add iodomethane (3.3 mL, 53.04 mmol) and slowly warm to RT. Quench the reaction mixture with methanol (5 mL) and dilute with water (100 mL). Extract with EtOAc (3×70 mL), dry (MgSO4) and concentrate and purify (Biotage system eluting with dichloromethane:methanol 50:1) to give desired compound as a white solid (2.3 g, 29% yield).

Workup

  1. customQuench the reaction mixture with methanol (5 mL)
  2. additiondilute with water (100 mL)
  3. extractionExtract with EtOAc (3×70 mL)
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate
  6. custompurify
  7. wash(Biotage system eluting with dichloromethane:methanol 50:1)

Sources & evidence

ORD record
ord-2423c662901644009a9345bbccbb9a00
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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