Reaction #337209

Reaction equation

5-bromopyridin-3-amine

toluene

sodium carbonate

phenylboronic acid

→

5-phenylpyridin-3-amine

Yield 13.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureto cool to room temperature for 16 hours
2. 2
   OtherThe reaction mixture was transferred to a separatory funnel
3. 3
   Otherpartitioned between ethyl acetate and water
4. 4
   WashThe aqueous phase was washed once more with ethyl acetate
5. 5
   Washthe combined organic phases were washed with brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   OtherThe residue was purified by column chromatography (80% ethyl acetate/hexanes)

Procedure

A mixture of 5-bromopyridin-3-amine (248 mg, 1.43 mmol), Pd(PPh3)4 (50.4 mg, 0.04 mmol), toluene (3 mL), sodium carbonate (2 M, 3 mL, 6 mmol), and phenylboronic acid (195 mg, 1.60 mmol) dissolved in ethanol (3 mL) was heated for 4 hours in an oil bath at 90° C. and allowed to cool to room temperature for 16 hours. The reaction mixture was transferred to a separatory funnel and partitioned between ethyl acetate and water. The aqueous phase was washed once more with ethyl acetate, and the combined organic phases were washed with brine and dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (80% ethyl acetate/hexanes) to afford 5-phenylpyridin-3-amine (31.9 mg, 0.19 mmol, 13% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 8.17-8.42 (m, 1 H), 8.02-8.20 (m, 1 H), 7.32-7.62 (m, 4 H), 7.25 (s, 1 H), 7.06-7.20 (m, 1 H). MS (LC/MS) R.T.=0.91; [M+H]+=171.09.

Source