Water → 2-(5-Bromo-4-cyano-2-fluorophenylamino)-4,4,4-trifluorobutanamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromo-4,5-difluorobenzonitrile	HCID 19261277	—
Reactant	2-Amino-4,4,4-trifluorobutanamide	HCID 44717372	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-(5-Bromo-4-cyano-2-fluorophenylamino)-4,4,4-trifluorobutanamide	HCID 67510681	45.1%

Reaction Steps

A solution of 2-bromo-4,5-difluorobenzonitrile (123 mg, 0.564 mmol), 2-amino-4,4,4-trifluorobutanamide (88 mg, 0.564 mmol) and DIEA (0.250 mL, 1.43 mmol) in DMSO (4 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-70% EtOAc in hexane to give 2-(5-bromo-4-cyano-2-fluorophenylamino)-4,4,4-trifluorobutanamide (90 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846928B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-825b92a45574448bb03e1722c1b2b6b6
Source note	uspto-grants-2014_09