Methyl iodide → HCID 68052600, compound

HRID 1685130Notes

Reaction equation

HRID 1685130 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[C:11]([C:23]([O:25][CH3:26])=[O:24])[NH:10][N:9]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+].[CH3:30]I>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[C:11]([C:23]([O:25][CH3:26])=[O:24])[N:10]([CH3:30])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 168937Lithium hydroxide, monohydrateHCID 68052597HCID 68052597, compound

Product 1

HCID 68052600HCID 68052600, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(4-bromophenyl)-4-(4-methoxybenzyloxy)-1H-pyrazole-5-carboxylate T-11 (10 g, 24 mmol) in anhydrous N,N-dimethylformamide (100 mL) cooled in an ice bath was added lithium hydroxide monohydrate (3 g, 71 mmol) and methyl iodide (10 g, 70 mmol). The reaction mixture was stirred at room temperature for 3 hours. The crude product was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude solid product was washed with hexane to afford the desired methyl 3-(4-bromophenyl)-4-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-5-carboxylate T-12 (7 g, 16 mmol).

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customSolvent was evaporated under reduced pressure
  4. washThe crude solid product was washed with hexane

Sources & evidence

ORD record
ord-2787ce404b934e34913d6e80483696c8
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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