Water → HCID 67120061, compound

HRID 242188Notes

Reaction equation

HRID 242188 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2[C:23]#[N:24])=[C:5]([CH3:25])[O:4][N:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2[C:23]#[N:24])=[C:5]([CH3:25])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67120023HCID 67120023, compound

Product 1

HCID 67120061HCID 67120061, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3,5-Dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbonitrile (12 mg, 0.036 mmol) was dissolved in CH2Cl2 (3 mL) and BBr3 (1 M solution in DCM, 0.3 mL, 0.28 mmol) was added. The mixture was stirred at room temperature over night. Water and DCM were added and the phases were separated. The organic phase was purified on a silica plug to give 5-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-3-propyl-1H-pyrazole-4-carbonitrile (5.4 mg, 47%).

Workup

  1. customthe phases were separated
  2. customThe organic phase was purified on a silica plug

Sources & evidence

ORD record
ord-6bd3aae65ce14353ab9a770ab75dfe63
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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