Sodium Carbonate → 2-Furan-2-yl-6-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-(Trifluoromethyl)phenylboronic acid	HCID 2734389	—
Reactant	[1,2,4]Triazolo[1,5-a]pyrazin-8-amine, 6-bromo-2-(2-furanyl)-	HCID 71401630	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Furan-2-yl-6-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine	HCID 11233248	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (50 mg, 0.179; see Examples 1 and 2), 4-trifluoromethyl-phenyl boronic acid (0.196 mmol), Pd(dppf)Cl2 (7 mg, 0.009 mmol), and aqueous Na2CO3 (2 M, 330 μL) in DMF (2 mL) was degassed under N2 and then heated (at around 100° C.) for overnight. The reaction was filtered and then purified by HPLC (C18, H2O:MeCN gradient). 1H NMR (300 MHz, DMSO-d6) δ 6.77 (dd, J=3.4, 1.8 Hz, 1H), 7.19 (dd, J=3.4, 0.8 Hz, 1H), 7.70 (br. s, 2H), 7.87 (d, J=8.2 Hz, 2H), 7.93 (dd, J=1.8, 0.7 Hz, 1H), 8.31 (d, J=8.2 Hz, 2H), 8.8 (s, 1H). MS: m/z 346 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07674791B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-89d1c4b68dea468eb13399318bdd4df4
Source note	uspto-grants-2010_03