Hexachloroethane → (6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-dimethyl-amine

Participants

Role	Name	HCID	Charge
Reactant	Hexachloroethane	HCID 6214	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	2-(5-Fluoropyridin-2-yl)-N,N-dimethylhydrazine carboxamide	HCID 86687062	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-dimethyl-amine	HCID 86687063	14.5%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of Intermediate 59a (590 mg, 2.98 mmol), Ph3P (1.56 g, 5.96 mmol) and Et3N (1.20 g, 11.9 mmol) in THF (40 mL) was added hexachloroethane (1.41 g, 5.96 mmol) and the mixture stirred at 60° C. for 9 h. The mixture was diluted with EtOAc (100 mL), washed with water, brine, dried (MgSO4) and then concentrated in vacuo. The residue was purified by FCC, using 0-10% (2M NH3 in MeOH) in DCM, then triturated with diethyl ether to give the title compound (78 mg, 14%). LCMS (Method 1): Rt 2.24 min, m/z 181 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315503B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-47dd794f969a4858b0a436f4fe9b0f42
Source note	uspto-grants-2016_04