Potassium Phosphate, Tribasic → [2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-(3-nitro-pyridin-4-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	4-Amino-3-nitropyridine	HCID 548803	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-Bromo-2-(5-chloro-2-fluoro-phenyl)-quinoline	HCID 67172712	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	2-Methyl-2-butanol	HCID 6405	—
Product	[2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-(3-nitro-pyridin-4-yl)-amine	HCID 67173069	—

Reaction Steps

10 g 4-Bromo-2-(5-chloro-2-fluoro-phenyl)-quinoline (cf. Example 5; M 336.59), and 4.13 g of 3-nitro-4-amino pyridine in 500 ml tert. amylalcohol were treated under argon with 272 mg Pd2(dba)3 (ABCR) and 0.69 g Xanthphos (ABCR) under basic conditions adjusted with 12.6 g K3PO4 at 117° C. external (100° C. internal temperature) for 6.5 hrs. Work-up with ethyl acetate extract washed with aqueous 5% KHSO4 solution (pH 2) and aqueous 5 NaHCO3 solution yielded after drying with Na2SO4, filtration and washings with methanol 6.6 g yellow powder of correct mass M+H+ 395 and Rt˜2.67 min and Rf˜0.44 in TLC on silica in petrolether/EE 2:1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987301B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-2841742e6ba749dc98ce64f057ea28a5
Source note	uspto-grants-2015_03