N-bromobutanimide → HCID 66869262, compound

HRID 250755Notes

Reaction equation

HRID 250755 reaction equation
[C:1]([C:4]1[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:6][N:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1)([OH:3])=[O:2].BrN1C(=O)C[CH2:23][C:22]1=O>CN(C=O)C.CCOC(C)=O>[CH2:22]([O:2][C:1]([C:4]1[C:5]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[N:6][N:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1)=[O:3])[CH3:23]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 39095983HCID 39095983, compound

Product 1

HCID 66869262HCID 66869262, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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. washwash with cooled water (5×10 mL)
  2. dry with materialdry (MgSO4)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-13cd04488efb41708056b170851dd1e6
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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