Toluene → 5-Nitro-2-phenylpyridine

A mixture of toluene (15 mL) and water (5 mL) was degassed with argon for 5 minutes. Sodium carbonate (0.80 g, 4.54 mmol) was added and the mixture was degassed with argon gas for 5 minutes. Phenyl boronic acid (0.59 g, 4.54 mmol) and 2-chloro-5-nitro-pyridine (0.6 g, 3.78 mmol) were added and the mixture was again degassed with argon gas for 5 minutes. Tetrakis palladium triphenyl phosphine (0.88 g, 0.76 mmol) was added and the mixture was degassed with argon gas for 5 minutes. The resulting mixture was heated to reflux for 3 hours. The mixture was then diluted with ethyl acetate, washed with water then brine solution. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford a residue which was purified by column chromatography using silica gel 60-120 mesh (5% ethyl acetate in hexane) to afford 0.5 g (66%) of 5-nitro-2-phenyl-pyridine. LCMS purity: 201 (M+1)+, 98.2%, 1H NMR (DMSO-d6): δ 9.5 (s, 1H), 8.55 (dd, 1H), 8.1 (m, 2H), 7.9 (d, 1H), 7.55 (m, 3H).

1. customwas degassed with argon for 5 minutes
2. customthe mixture was degassed with argon gas for 5 minutes
3. customthe mixture was again degassed with argon gas for 5 minutes
4. customthe mixture was degassed with argon gas for 5 minutes
5. temperatureThe resulting mixture was heated
6. temperatureto reflux for 3 hours
7. additionThe mixture was then diluted with ethyl acetate
8. washwashed with water
9. dry with materialThe organic layer was dried over sodium sulphate
10. concentrationconcentrated under reduced pressure
11. customto afford a residue which
12. customwas purified by column chromatography

ORD record

ord-504887177914447599624e7291f7920b

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039463B2