Sodium Carbonate → 4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3,4-Dichlorobenzeneboronic acid	HCID 2734330	—
Reactant	4-Bromo-2,6-diaminopyridine	HCID 11435393	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 44119782	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine	HCID 22629723	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 40.5 mg (0.21 mmol) 2,6-diamino-4-bromo-pyridine, 90.5 mg (0.47 mmol) 3,4-dichloro-phenyl-boronic acid, 7.8 mg (0.01 mmol) Dichloro(1,1′-bis(diphenylphosphino) ferrocene)palladium (II) dichloromethane adduct and 0.3 ml 2M Na2CO3 in 1 ml dimethoxyethane was heated to 80° C. for 17 h. The mixture was filtered over silica washed with MeOH/DCM and concentrated. The residue was taken up in 1 ml DMF and the totle compound was purified by reversed phase column chromatography eluting wit an acetonitrile/water gradient to yield 29 mg (52%), MS m/e (%): 254 M+ (100).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06355653B1
Source dataset	uspto-grants-2002_03
ORD ID	ord-77b5c055a48d483a9344df34f173807e
Source note	uspto-grants-2002_03