Cesium carbonate → HCID 86690872, compound

A solution of 5-3 (1.92 g, 5.91 mmol) in DMF (15 mL) was added with cesium carbonate (2.41 g, 7.39 mmol). The reaction mixture was heated at 50° C. for 60 min and added with 5-bromo-2-nitropyridine (24-1, 1.80 g). The reaction mixture was heated at 50° C. for 4.0 h. The solution was quenched with water (40 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3) to give 24 (1.76 g) in 67% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.78 (d, 2 H), 8.42 (d, 1 H), 8.33 (d, 1 H), 7.96 (d, 2 H), 7.63 (m, 1 H), 7.21 (s, 1 H), 7.01 (s, 2 H), 2.08 (s, 6 H), ESI-MS=m/z 447.5 (M+H)+.

1. temperatureThe reaction mixture was heated at 50° C. for 4.0 h
2. customThe solution was quenched with water (40 mL)
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3)

ORD record

ord-59f79e2287f24700840204c3be231266

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999983B2