Morpholine → 2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole

Participants

Role	Name	HCID	Charge
Reactant	Morpholine	HCID 8083	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	6-bromo-2-(1-methylethyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole	HCID 66976896	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole	HCID 66976960	77%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 6-bromo-2-(1-methylethyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole (2.05 g), morpholine (1.26 g), Pd2(dba)3 (0.46 g), Cs2CO3 (2.36 g) and X-Phos (0.41 g) in dioxane (30 mL) was degassed with nitrogen and then stirred at 80° C. overnight. The mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was then purified by silica gel chromatography eluted with (EtOAc:petroleum ether=1:1) to afford the desired product as a yellow solid (1.6 g, 77%). LC-MS: m/e=431 [M+1]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09062003B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-b79dc438b85d4848ac07a0e96d966ab5
Source note	uspto-grants-2015_06