Ethylenediamine → 4-Fluoro-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-yl]-benzamide

Into a 50 mL 3-necked round bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1-(5-bromo-pyrazin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (iv) (100 mg, 0.27 mmol) in 1,4-dioxane (30 mL). To this was added 4-fluorobenzamide (80 mg, 0.58 mmol), K3PO4 (250 mg, 1.18 mmol), CuI (10 mg, 0.05 mmol) and ethane-1,2-diamine (EDA) (5 mg, 0.08 mmol). The resulting solution was stirred at reflux overnight. The reaction progress was monitored by TLC (EtOAc/PE=1:2). When the reaction had gone to completion, the mixture was filtered to remove the solid components, then concentrated under vacuum. The residue was dissolved in EtOAc, then washed with water. The organic layer was dried over Na2SO4, then concentrated to yield a crude product.

1. customInto a 50 mL 3-necked round bottom flask, purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperatureat reflux overnight
4. filtrationthe mixture was filtered
5. customto remove the solid components
6. concentrationconcentrated under vacuum
7. dissolutionThe residue was dissolved in EtOAc
8. washwashed with water
9. dry with materialThe organic layer was dried over Na2SO4
10. concentrationconcentrated

ORD record

ord-e1af3749b2cd4a9f93382253b34a2f61

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324219B2