تفاعل #337209

معادلة التفاعل

5-bromopyridin-3-amine

toluene

sodium carbonate

phenylboronic acid

→

5-phenylpyridin-3-amine

المردود 13.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to room temperature for 16 hours
2. 2
   أخرىThe reaction mixture was transferred to a separatory funnel
3. 3
   أخرىpartitioned between ethyl acetate and water
4. 4
   غسيلThe aqueous phase was washed once more with ethyl acetate
5. 5
   غسيلthe combined organic phases were washed with brine
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe residue was purified by column chromatography (80% ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر