2-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone Oxime → HCID 67255182, compound

HRID 1190858Notes

Reaction equation

HRID 1190858 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:10]O)[CH:3]=1>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:8]=[C:4]2[CH:3]=1

Participants

3

Reactant 1

HCID 866713742-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone Oxime

Product 1

HCID 67255182HCID 67255182, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

7.82 g (25.50 mmol) of 2-(4-bromopyridin-2-yl)-1-(4-fluorophenyl)ethanone oxime are placed in a round-bottomed flask and dissolved in 400 mL of 1,2-dichloroethane. An O-(mesitylenesulfonyl)hydroxylamine solution (0.27 M in 1,2-dichloroethane—compound obtained according to the protocol described in step 1.3) is added dropwise to the medium cooled to about 0° C. After the addition, the medium is stirred at room temperature for 1 hour 30 minutes. The medium is then diluted with 200 mL of water and 200 mL of sodium hydroxide solution (1N). The two-phase medium is stirred and the phases are then separated by settling. The organic phase is separated out and the aqueous phase is then extracted 4 times with 200 mL of dichloromethane. The organic phases are then combined, dried over sodium sulfate and filtered. 15 g of silica are then added to the filtrate, and the resulting mixture is then concentrated under reduced pressure. The powder obtained is used as solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and dichloromethane (1/1). 5.06 g (68%) of compound are obtained in the form of a fleecy white powder.

Sources & evidence

ORD record
ord-c572601ae15145aeb87cd3bfd4afaabe
Source dataset
uspto-grants-2014_03
Patent number
US08680096B2

Reaction notes

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