Water → 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 242192Notes

Reaction equation

HRID 242192 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=2[F:15])[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18].B(Br)(Br)Br.O>C(Cl)Cl>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[F:15])[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 671200265-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 671200435-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrileYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude 5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (256 mg, 1.04 mmol) from above was dissolved in CH2Cl2 (25 mL) and BBr3 (1 M solution in DCM, 5 mL, 5.0 mmol) was added and stirred over night. CH2Cl2 and water were added and the phases separated. The aqueous phase was again extracted with EtOAc/CH2Cl2 (1:1). The solution was dried using a phase separator and concentrated under reduced pressure to give 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (217 mg, 76%), which was used as such in the next step.

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was again extracted with EtOAc/CH2Cl2 (1:1)
  3. customThe solution was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89211d346f4346448acda60c179e0096
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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