2,6-Dimethylaniline → HCID 58114883, compound

Participants

Role	Name	HCID	Charge
Reactant	2,6-Dimethylaniline	HCID 6896	—
Reactant	2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl	HCID 2734217	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	HCID 58114889	HCID 58114889	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	HCID 58114883	HCID 58114883	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 8-bromo-2-(1-naphthyl)quinoline (2.03 g, 6 mmol), 2,6-dimethylaniline (0.83 mL, 6.9 mmol), Pd(dba)2 (0.072 g, 0.12 mmol), L=(N-[2′-(dicyclohexylphosphino)[1,1′-biphenyl]-2-yl]-N,N-dimethylamine) (0.094 g, 0.24 mmol), NaOtBu (0.72 g, 7.2 mmol) and toluene (15 mL) is stirred for 8 h under an argon atmosphere at 100° C. in an oil bath. The mixture is then poured into water and extracted with benzene (3×50 mL). The combined organic phase is washed with water and brine, and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 2:1). Yield: 1.59 g (71%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07858718B1
Source dataset	uspto-grants-2010_12
ORD ID	ord-6f1addbb5548478999e88e7a47ec1d12
Source note	uspto-grants-2010_12