반응 #337209

반응 방정식

5-bromopyridin-3-amine

toluene

sodium carbonate

phenylboronic acid

→

5-phenylpyridin-3-amine

수율 13.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도to cool to room temperature for 16 hours
2. 2
   기타The reaction mixture was transferred to a separatory funnel
3. 3
   기타partitioned between ethyl acetate and water
4. 4
   세척The aqueous phase was washed once more with ethyl acetate
5. 5
   세척the combined organic phases were washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue was purified by column chromatography (80% ethyl acetate/hexanes)

실험 절차

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.

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