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

HRID 1410166Notes

Reaction equation

HRID 1410166 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>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

4

Reactant 2

HCID 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 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-amino-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (256 mg, 1.0 mmol) was dissolved in CH2Cl2 (25 mL) and BBr3 (1 M solution in DCM, 4.91 mL, 4.91 mmol) was added and stirred at room temperature over night. The reaction was quenched using water, extracted with CH2Cl2, and dried using a phase separator. Concentration gave 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (232.1 mg, 100%) which was used as such in the next step.

Workup

  1. customThe reaction was quenched
  2. extractionextracted with CH2Cl2
  3. customdried
  4. concentrationConcentration

Sources & evidence

ORD record
ord-bddde153ac24495daaf57fc9922e17bc
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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