Reaktion #337209

Reaktionsgleichung

5-bromopyridin-3-amine

toluene

sodium carbonate

phenylboronic acid

→

5-phenylpyridin-3-amine

Ausbeute 13.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle