Hydrochloric Acid → HCID 39095983, compound

HRID 250754Notes

Reaction equation

HRID 250754 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:9]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)=[O:7])C.C(#N)C.Cl>CO>[C:6]([C:8]1[C:9]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 66869262HCID 66869262, compound

Product 1

HCID 39095983HCID 39095983, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Add a solution of NaOH (15%, 6 mL) to a solution of 4-ethoxycarbonyl-3-(4-fluorophenyl)-1-tert-butyl-1H-pyrazole (0.350 g, 1.2 mmol) in MeOH (3 mL) and then add acetonitrile (1 mL). Stir the mixture at 50° C. for 3 h, cool to RT and add HCl (10%) until the pH=3. Extract the mixture with EtOAc (3×100 mL). Combine the organic layers and wash with brine (100 mL), dry (MgSO4) and concentrate to provide 4-carboxy-3-(4-fluorophenyl)-1-tert-butyl-1H-pyrazole as a yellow solid (0.320 g), MS (ESi+): 229.1 (M+H)+. Next treat a solution of 4-carboxy-3-(4-fluorophenyl)-1-tert-butyl-1H-pyrazole (0.315 g, 1.2 mmol) in DMF (15 mL) previously degassed with N-bromosuccinimide (0.235 g, 1.32 mmol) at RT for about 18 h. Dilute the mixture with EtOAc (80 mL) and wash with cooled water (5×10 mL), dry (MgSO4), and concentrate to provide the desired compound as yellow solid (0.262 g, 73% yield).

Workup

  1. temperaturecool to RT
  2. extractionExtract the mixture with EtOAc (3×100 mL)
  3. washCombine the organic layers and wash with brine (100 mL)
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b5069f36d9e74c619e1be285aad31f38
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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