Phenylboronic Acid → (2-Methoxy-phenyl)-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	(8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine	HCID 67481519	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	(2-Methoxy-phenyl)-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine	HCID 67478857	—

Reaction Steps

(2-Methoxy-phenyl)-(8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine was prepared from (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(2-methoxy-phenyl)-amine (50.0 mg, 0.157 mmol) and phenylboronic acid (21.0 mg, 0.172 mmol) with Pd(dppf)Cl2 (0.012 g) as the catalyst in a manner analogous to Step 2c and was isolated as a white solid (0.012 g, 24%). MP=155-157° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.44 (dd, J=6.6, 0.9 Hz, 1H), 8.40 (dd, J=8.0, 1.4 Hz, 1H), 8.02-7.97 (m, 2H), 7.61 (s, 1H), 7.56 (dd, J=7.4, 0.9 Hz, 1H), 7.55-7.50 (m, 2H), 7.45-7.40 (m, 1H), 7.07-7.02 (m, 1H), 6.98-6.88 (m, 3H), 3.91 (s, 3H). MS=317 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08633173B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-1e193c1320df4c0ebc638b17722261e4
Source note	uspto-grants-2014_01