Water → 6,6'-bis(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	9-(4-(5-bromopyridin-2-yl)phenyl)-9H-carbazole	HCID 66799588	—
Reactant	9-(4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenyl)-9H-carbazole	HCID 66801433	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6,6'-bis(4-(9H-carbazol-9-yl)phenyl)-3,3'-bipyridine	HCID 56943730	180%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 6 (4.11 g, 10.3 mmol), 7 (4.60 g, 10.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.595 g, 0.515 mmol), Na2CO3 (5.41 g, 51.0 mmol), H2O (55 mL) and THF (92 mL) was degassed with argon for about 1 h while stirring. The stirring reaction mixture was then maintained under argon at about 80° C. for about 18 h. Upon confirming consumption of the starting materials by TLC (SiO2, 49:1 dichloromethane-acetone), the reaction was cooled to RT, filtered and filtrant washed with EtOAc and H2O to afford 8 (5.92 g, 90%) as an off-white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09328086B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-4a6c1509b92a434e8df8481f6a34bfe6
Source note	uspto-grants-2016_05