2-Bromopyridine → tert-Butyl (2-oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Temperatur

100 °C

A mixture of tert-butyl (2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step A (1.75 g, 7.05 mmol), 2-bromopyridine (3.36 mL, 35.2 mmol), copper powder (1.57 g, 24.7 mmol), CuCl (140 mg, 1.41 mmol), and KOAc (2.08 g, 21.1 mmol) in pyridine (30 mL) was heated at 100° C. for 3 h. The cooled mixture was partitioned between EtOAc (150 mL) and 10% aqueous citric acid (100 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=326 (M+1).

1. customThe cooled mixture was partitioned between EtOAc (150 mL) and 10% aqueous citric acid (100 mL)
2. dry with materialthe organic layer was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by silica gel chromatography
6. washeluting with a gradient of hexane

ORD-Eintrag

ord-24d366521ee04cf986e7f240afd16a3c

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08173655B2