Hydrochloric Acid → HCID 178487824, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Diethylene Glycol Monomethyl Ether	HCID 8134	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Chloro-6-methoxy-3-methylquinoline	HCID 4914664	—
Reactant	HCID 178514828	HCID 178514828	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Sodium Hydroxide	HCID 14798	—
Product	HCID 178487824	HCID 178487824	84%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(1H-tetrazol-5-yl)phenylboronic acid (91.2 mg, 0.482 mmol), K2CO3 (199 mg, 1.45 mmol), and PdCl2(dppf) (17.6 mg, 0.024 mmol) was added 7 mL of DEGME and 3 mL of H2O under argon. The mixture was stirred at 150° C. in a microwave reactor for 1.5 hours. The crude mixture was diluted with 1N NaOH (10 mL) and slowly acidified to a pH of 4.0 using conc. HCl. The solids were filtered to yield 128 mg (84% yield) of desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08921562B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-cb652c88da8b41dcb3bce3a4c48637aa
Source note	uspto-grants-2014_12