Potassium Phosphate, Tribasic → N-(4-methoxybenzyl)-3-(trifluoromethyl)-[2,3'-bipyridin]-5-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	3-(Diethylboryl)pyridine	HCID 642851	—
Reactant	6-Chloro-N-((4-methoxyphenyl)methyl)-5-(trifluoromethyl)-3-pyridinamine	HCID 25020033	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	N-(4-methoxybenzyl)-3-(trifluoromethyl)-[2,3'-bipyridin]-5-amine	HCID 67374880	73.2%

Reaction Conditions

Temperature	105 °C

Reaction Steps

To a solution of 6-chloro-N-(4-methoxybenzyl)-5-(trifluoromethyl)pyridin-3-amine (Intermediate 1, Step 3, 1.2 g, 3.8 mmol) and 3-(diethylboryl)pyridine (0.613 g, 4.17 mmol) in 1,4-dioxane (100 mL) was added K3PO4(2.52 g, 9.48 mmol). The mixture was degassed then flushed with nitrogen before Pd2(dba)3 (173 mg, 0.02 mmol) and Xantphos (0.218 mg, 0.04 mmol) were added. The mixture was heated at 105° C. overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel using EtOAc/PE=1/to afford 1 g of N-(4-methoxybenzyl)-3-(trifluoromethyl)-[2,3′-bipyridin]-5-amine.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09108944B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-a0a151ac70ae4112b94d11d0a92f2d41
Source note	uspto-grants-2015_08