Water → HCID 178418951, compound

HRID 9875Notes

Reaction equation

HRID 9875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:19][C:10]1[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 121061684-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyridine

Product 1

HCID 178418951HCID 178418951, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Fluorophenyl)-4-(pyridin-4-yl)pyrazole (6.0 g (25 mmol), prepared as described in WO 00/31063) was dissolved in dimethylformamide (60 ml). To the solution was added N-bromosuccinimide (8.93 g, 50 mmol), and the resulting mixture was stirred at room temperature for 3 days. At the end of this time, water was added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with diethyl ether, to give the title compound (5.73 g) as a white powder (yield 72%).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-111964c177044a658f9701d6362bd642
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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