Boron tribromide → HCID 67120064, compound

HRID 242204Notes

Reaction equation

HRID 242204 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]1[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:14]=2[F:21])[N:11]=[C:10]([CH3:22])[C:9]=1[C:23]#[N:24].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]1[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[F:21])[N:11]=[C:10]([CH3:22])[C:9]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68155867HCID 68155867, compound

Product 1

HCID 67120064HCID 67120064, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(1,3-Dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (20 mg, 0.06 mmol) was dissolved in CH2Cl2 (3 mL) and BBr3 (1 M solution on DCM, 0.3 mL, 0.3 mmol) was added and stirred at room temperature over night. The reaction was quenched using water and extracted with CH2Cl2. Concentration and purification using preparative HPLC gave 5-(1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (10 mg, 53%). Also 5-(5-bromo-1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (7 mg) was isolated.

Workup

  1. customThe reaction was quenched
  2. extractionextracted with CH2Cl2
  3. concentrationConcentration and purification

Sources & evidence

ORD record
ord-c23069779e8845599cf97a120b33ffb5
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

Loading…