Potassium Carbonate → Ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylate

HRID 1440799Notes

Reaction equation

HRID 1440799 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]#[N:34])=[CH:23][CH:22]=1>CN(C)C=O>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:1][C:2]2[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=2)=[CH:26][CH:25]=1)#[N:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 252927ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 15338339Ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 3-amino-1-methylpyrazole-4-carboxylate (P. Schmidt et al. Hel. Chim. Acta., 1959, 41, 349.) (2.30 g) and potassium carbonate in N,N-dimethylformamide (70 ml), was added portionwise 4-bromomethyl-2'-cyanobiphenyl (4.81 g). The solvent was distilled under reduced pressure. To the residue was added ice-water and an aqueous solution of potassium carbonate. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give crude crystals, which were recrystallization from ethyl acetate-isopropylether to afford the title compound as white crystals (3.7 g, 76%), m.p. 151°-152° C.

Workup

  1. distillationThe solvent was distilled under reduced pressure
  2. additionTo the residue was added ice-water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto give crude crystals, which
  8. customrecrystallization from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-9e28ccf1f1c3486092b69c784f0653f5
Source dataset
uspto-grants-1996_03
Patent number
US05500427

Reaction notes

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