Sodium Carbonate → 2-[4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]-benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 3570229	—
Reactant	7-(2-Chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine	HCID 11335561	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	2-[4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]-benzonitrile	HCID 9907172	4%

Reaction Steps

7-(2-Chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine was coupled with 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile in the presence of tetrakis(triphenylphosphine)palladium(0) and sodium carbonate, at 80° C. in aqueous 1,2-dimethoxyethane, to give the title compound in 4% yield: 1H NMR (360 MHz, CDCl3) δ 7.60 (1H, td, J 1.1, 7.7), 7.78 (1H, td, J 1.1, 7.7), 7.89 (1H, dd, J 1.1, 7.7), 7.97 (1H, dd, J 7.0, 0.7), 8.13 (1H, dd, J 1.8, 5.3), 8.65 (1H, d, J 0.7), 8.84 (1H, s), 8.94 (1H, s), 8.99 (1H, dd, J 0.7, 5.3).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07176203B2
Source dataset	uspto-grants-2007_02
ORD ID	ord-a85ff706bf0648e6ab9541b1056b7af9
Source note	uspto-grants-2007_02