Aniline → [4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyridin-2-yl]phenyl-amine

Participants

Role	Name	HCID	Charge
Reactant	Aniline	HCID 6115	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	2-Bromo-4-(5-methyl-3-phenyl-isoxazol-4-yl)-pyridine	HCID 23435665	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane ethylacetate	HCID 21226138	—
Product	[4-(5-Methyl-3-phenyl-isoxazol-4-yl)-pyridin-2-yl]phenyl-amine	HCID 69143504	61.1%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a stirred solution of the above Compound 17a (20 mg, 0.063 mmol), aniline (7.0 μL, 0.076 mmol) and BINAP (5.6 mg, 0.009 mmol) in toluene (0.6 mL) at 25° C. was added Pd2(dba)3 (2.7 mg, 0.003 mmol) followed by NaOtBu (9.1 mg, 0.095 mmol). The solution was heated to 80° C. for 2 h. The solution was cooled, filtered and concentrated. Preparative thin layer chromatography (SiO2, 5% EtOAc/CH2Cl2) provided the title compound (12.6 mg, 0.0385 mmol, 61%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07169798B2
Source dataset	uspto-grants-2007_01
ORD ID	ord-6755966212194c4aa190803784fffaf9
Source note	uspto-grants-2007_01