N-methoxy-N,1-dimethyl-1H-pyrazole-4-carboxamide → 1-(1-methyl-1H-pyrazol-4-yl)-2-phenylethanone

HRID 1844523Notes

Reaction equation

HRID 1844523 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:11])[CH:10]=1)=[O:5].[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH3:11][N:9]1[CH:10]=[C:6]([C:4](=[O:5])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[N:8]1

Participants

4

Reactant 2

HCID 58477471N-methoxy-N,1-dimethyl-1H-pyrazole-4-carboxamideHCID 178418336HCID 178418336, compound

Product 1

HCID 155619131-(1-methyl-1H-pyrazol-4-yl)-2-phenylethanoneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N,1-dimethyl-1H-pyrazole-4-carboxamide (4.6 g, 27.2 mmol) in anhydrous THF (50 mL) was added benzylmagnesium chloride (2.0 M in THF, 16.7 mL, 32.6 mmol) at −78° C. under N2, then stirred at the same temperature for 3 hours. The mixture was quenched with saturated NH4Cl solution, followed by a standard aqueous/EtOAc procedure. The crude was purified by silica gel column chromatography (PE:EtOAc=10:1) to give Intermediate 4 (4.0 g, yield 74%).

Workup

  1. customThe mixture was quenched with saturated NH4Cl solution
  2. customThe crude was purified by silica gel column chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-06dd067e6bbc4849b112ad28f36b60d6
Source dataset
uspto-grants-2015_02
Patent number
US08946434B2

Reaction notes

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