Potassium Carbonate → ethyl 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrazole-5-carboxylate

HRID 1630662Notes

Reaction equation

HRID 1630662 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[N:4]=[N:5][NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([C:20]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:22]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:21]=1)=[O:19]>C(#N)C>[Cl:36][C:35]1[C:30]([N:22]2[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:24][C:20]([C:18](=[O:19])[CH2:17][N:5]3[N:6]=[N:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]3)=[N:21]2)=[N:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4217082H-Tetrazole, 5-(trifluoromethyl)-, sodium salt (1:1)HCID 86661386ethyl 3-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 66587559ethyl 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1.24 g (2.04 mmol) of 5-(trifluoromethyl)-2H-tetrazole and 348 mg (2.52 mmol) of potassium carbonate were initially charged in 15 ml of acetonitrile and stirred at RT for 15 min. 693 mg (1.57 mmol) of ethyl 3-(bromoacetyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, dissolved in 5 ml of acetonitrile, were added, and the reaction mixture was stirred at 70° C. for 5 min. Half of the solvent was distilled off, the residue was diluted with 80 ml of water and the mixture was extracted twice with dichloromethane. The combined organic phases are washed with sodium chloride solution, dried over sodium sulphate and concentrated. The desired product was isolated by chromatographic purification.

Workup

  1. additionwere added
  2. stirringthe reaction mixture was stirred at 70° C. for 5 min
  3. distillationHalf of the solvent was distilled off
  4. additionthe residue was diluted with 80 ml of water
  5. extractionthe mixture was extracted twice with dichloromethane
  6. washThe combined organic phases are washed with sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9553a1d4656444319cf12a01fec40b95
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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