Sodium Carbonate → HCID 57643118, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-Methoxypyridine-3-boronic Acid	HCID 2763087	—
Reactant	N-(7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N′-ethylurea	HCID 57643071	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 57643118	HCID 57643118	—

Reaction Steps

Compound 4, prepared as in Example 1, (120 mg, 0.42 mmol) was dissolved in dioxane (5 mL), to which was added Na2CO3 (0.50 mL of a 2 M aqueous solution) and 3-methoxy-5-pyridineboronic acid (107 mg, 0.70 mmol). Pd(dppf)Cl2 (38 mg) was added last, and the mixture heated under nitrogen at reflux for 15 h. The reaction solvent was removed and the residue filtered through a plug of silica gel (gradient 2-5% MeOH/CH2Cl2 as eluant) to give a solid which was triturated with Et2O. 1-Ethyl-3-[7-(6-methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea was isolated mp. 230-233° C. Anal. calcd for C15H16N6O2: C, 57.7; H, 5.2; N, 26.9. Found: C, 57.6; H, 5.2; N, 26.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07524860B2
Source dataset	uspto-grants-2009_04
ORD ID	ord-1c30c76f0615471381f6c06382bdeb0b
Source note	uspto-grants-2009_04