2-Chloro-4-fluorobenzoyl chloride → 4-(2-chloro-4-fluorobenzoyl)-5-(2,6-difluorophenyl)-1-methyl-1H-pyrazole-3-carbonitrile

HRID 406599Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[C:24]1[N:28]([CH3:29])[N:27]=[C:26]([C:30]#[N:31])[CH:25]=1>ClCCCl.ClC(Cl)C>[Cl:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:25]1[C:26]([C:30]#[N:31])=[N:27][N:28]([CH3:29])[C:24]=1[C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[F:16])=[O:9]

Participants

Conditions

Temperature: 180 °C

Procedure

To a mixture of aluminum chloride (0.18 g, 1.36 mmol) in 1,2-dichloroethane (2 mL) was added a mixture of 2-chloro-4-fluorobenzoyl chloride (0.26 g, 1.36 mmol) and 5-(2,6-difluorophenyl)-1-methyl-1H-pyrazole-3-carbonitrile (i.e. the product of Step B) (0.15 g, 0.68 mmol) in dichloroethane (1 mL). The reaction mixture was heated at 180° C. in a Biotage Initiator™ microwave apparatus for 30 minutes. The resulting mixture was poured directly onto a Varian Bond Elute SIC) column and eluted with methylene chloride followed by 30% ethyl acetate in hexanes to provide the title compound, a compound of the present invention, as a solid (0.07 g).

Workup

additionwas added
additionThe resulting mixture was poured directly onto a Varian Bond
washElute SIC) column
washeluted with methylene chloride

Sources & evidence

ORD record: ord-9c209cf174304474b3653d497eb71ea4
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754115B2

Reaction notes

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