反応 #928102

反応方程式

5-bromo-7-azaoxindole

phenylboronic acid

sodium carbonate

lithium chloride

→

5-phenyl-7-azaoxindole

収率 51.4%

溶媒

chloroform

toluene

ethanol

diethyl ether

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   洗浄washed with brine (20 ml)
3. 3
   抽出The aqueous layer was thoroughly extracted with chloroform
4. 4
   乾燥The combined organic layers were dried over anhydrous MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated under vacuum
7. 7
   その他to give crude product

実験手順

To a stirred mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) and phenylboronic acid (183 mg, 1.5 mmol) in toluene (6 ml) and ethanol (6 ml) were added 1 M sodium carbonate solution (2.5 ml, 2.5 mmol), lithium chloride (127 mg, 3 mmol) and dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmol) under N2 atmosphere. The reaction mixture was heated to reflux at 95° C. for 18 hours. The reaction mixture was diluted with chloroform (50 ml) and washed with brine (20 ml). The aqueous layer was thoroughly extracted with chloroform. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with diethyl ether yielded 5-phenyl-7-azaoxindole as a yellow solid (108 mg, 51.4%). 1H NMR (DMSO-d6): δ11.04 (s, 1H), 8.32 (s, 1H), 7.83 (s, 1H), 7.60 (d, 2H, J=7.4 Hz), 7.44 (t, 2H, J=7.4 Hz), 7.32 (t, 1H, J=7.4 Hz), 3.58 (s, 2H). MS (−ve APCI): 210 (48, M+), 209 (100, M−H).

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