N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide → 1-[1-[(4-Methoxyphenyl)methyl]-1H-pyrazol-4-yl]-1-propanone

HRID 1520194Notes

Reaction equation

HRID 1520194 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CON(C)[C:8]([C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:14]=1)=[O:9]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:13]2[CH:14]=[C:10]([C:8](=[O:9])[CH2:1][CH3:2])[CH:11]=[N:12]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 86642328N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamideHCID 178418443HCID 178418443, compound3×

Product 1

HCID 674344971-[1-[(4-Methoxyphenyl)methyl]-1H-pyrazol-4-yl]-1-propanoneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 2 Step 2: Ethylmagnesium bromide (3N, 37.2 mmol, 12.4 mL) was added dropwise at room temperature to a solution of N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g) in THF (80 mL) and the reaction mixture was stirred for 1 hour. Then ethylmagnesium bromide (3N, 37.2 mmol, 12.4 mL) was added and the reaction mixture was stirred for 1 hour. Finally some more ethylmagnesium bromide (3N, 74.4 mmol, 24.8 mL) was added and the reaction mixture was stirred for 1.5 hour at 50° C. The reaction was quenched with HCl (1 N, 300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (32.7 mmol, 8.00 g, 97%) as a yellow oil.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour
  2. stirringthe reaction mixture was stirred for 1.5 hour at 50° C
  3. customThe reaction was quenched with HCl (1 N, 300 mL)
  4. extractionthe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-75b67f8e2d2d4c6f84cf009cca1c2c3e
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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