Cesium carbonate → 2-Chloro-N-(2-(pyrimidin-2-yl)phenyl)-5-(trifluoromethyl)pyridin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	2-Chloro-4-iodo-5-(trifluoromethyl)pyridine	HCID 2773791	—
Reactant	2-(2-Pyrimidinyl)benzenamine	HCID 22493255	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Chloro-N-(2-(pyrimidin-2-yl)phenyl)-5-(trifluoromethyl)pyridin-4-amine	HCID 58154965	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

The mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (142 mg, 0.46 mmol), 2-(pyrimidin-2-yl)aniline (78 mg, 0.46 mmol), Pd2(dba)3 (23 mg, 0.025 mmol), xantphos (23 mg, 0.040 mmol) and cesium carbonate (325 mg, 1.0 mmol) in dioxane (4.5 ml) was microwave heated in a Biotage Initiator microwave synthesizer at 130° C. for 30′. The solvent was removed and the residue was purified by preparative HPLC (0.1% TFA in water/acetonitrile gradient) to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08501763B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-f6a1e131383f4ff08917440ab7399276
Source note	uspto-grants-2013_08