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

Temperature

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 record

ord-632af1b1ce7c4470878b675b602e97e1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071771B2