Toluene → 5-Phenyl-2-pyridinamine

A mixture of toluene (15 mL) and water (5 mL) was degassed with argon gas for 5 minutes. Sodium carbonate (481 mg, 4.5 mmol) was added and the resulting mixture was again degassed with argon gas for 5 minutes. Phenyl boronic acid (353 mg, 2.7 mmol) and 5-iodo-pyridin-2-ylamine (500 mg, 2.27 mmol) were added and the mixture was again degassed with argon gas for 5 minutes. Tetrakis palladium triphenyl phosphine (525 mg, 4.5 mmol) was then added and the mixture was again 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 and washed with water followed by brine solution. The ethyl acetate layer was collected, dried over sodium sulphate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel 60-120 mesh (35% ethyl acetate in hexane) to afford 10 mg (28%) of 5-phenyl-pyridin-2-ylamine. LCMS: 171.09 (M+1)+, 60.5%.

1. customwas degassed with argon gas for 5 minutes
2. customthe resulting mixture was again degassed with argon gas for 5 minutes
3. customthe mixture was again degassed with argon gas for 5 minutes
4. customthe mixture was again 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. customThe ethyl acetate layer was collected
10. dry with materialdried over sodium sulphate
11. concentrationconcentrated under reduced pressure
12. customThe resulting residue was purified by column chromatography

ORD record

ord-6a1e612d62cd4b5699233e29d581885b

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039463B2