1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → [8-(4-Chloro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

Participants

Role	Name	HCID	Charge
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Phenolate Sodium	HCID 4445035	—
Reactant	1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine	HCID 58397876	—
Reactant	2-Bromo-8-(4-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridine	HCID 67343447	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[8-(4-Chloro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine	HCID 53353913	—

Reaction Steps

Through a suspension of 1-(3-methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine (40 mg, 202 μmol), 2-bromo-8-(4-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (74.7 mg, 242 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (9.34 mg, 16.1 μmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (8.35 mg, 8.07 μmol) and sodium phenoxide (35.1 mg, 303 μmol) in dry dioxane (3 mL) was bubbled argon for 5 minutes. The mixture was then irradiated at 150° C. for 60 minutes. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as an off-white foam (42 mg, 49%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08486967B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-1e7ac74acf4e4d82bcb0f8b2bed4d28e
Source note	uspto-grants-2013_07