4-Methoxybenzyl bromide → 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbonitrile

HRID 1055630Notes

Reaction equation

HRID 1055630 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]#[N:7])[CH:3]=[N:2]1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH:5]=[C:4]([C:6]#[N:7])[CH:3]=[N:2]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1650214-Methoxybenzyl bromideHCID 5644491H-Pyrazole-4-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 866909571-(4-Methoxybenzyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 1 g (10.7 mmol) of 1H-pyrazole-4-carbonitrile and 2.4 g (11.8 mmol) of 4-methoxybenzyl bromide were initially charged in 22 ml of THF. 1.3 g (11.8 mmol) of potassium tert-butoxide were added a little at a time, and the reaction was stirred at RT overnight. The precipitated solid was then filtered off, and the mother liquor was freed from the solvent on a rotary evaporator. The residue was dissolved in ethyl acetate and the solution was washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. This gave 2 g (87% of theory) of the title compound, which was used without further purification for the subsequent step.

Workup

  1. filtrationThe precipitated solid was then filtered off
  2. customthe mother liquor was freed from the solvent on a rotary evaporator
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis gave 2 g (87% of theory) of the title compound, which was used without further purification for the subsequent step

Sources & evidence

ORD record
ord-4a45050454c04afcbf70a54ef9a0d1c8
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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