4-Chloro-2-fluoro-1-iodobenzene → 4-(4-chloro-2-fluorophenyl)-5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine

Participants

Role	Name	HCID	Charge
Reactant	4-Chloro-2-fluoro-1-iodobenzene	HCID 2736562	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine	HCID 66613369	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Product	4-(4-chloro-2-fluorophenyl)-5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine	HCID 66614225	—

Reaction Conditions

Temperature	180 °C

Reaction Steps

A mixture of 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine (i.e. the product of Step F) (7.07 g, 23.8 mmol), 4-chloro-2-fluoroiodobenzene (256 μL, 2.0 mmol), sodium tert-butoxide (0.192 g, 2.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (0.117 g, 0.16 mmol) in toluene (5 mL) was heated at 180° C. in a Biotage Initiator™ microwave apparatus for 1 h. The resulting material was purified by flash chromatography on a silica gel (40 g), Varian Bond Elute SIC) column (30% ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a dark purple/brown oil (164 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09131693B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-150d66f2f9914f2c8d45606212893ace
Source note	uspto-grants-2015_09