反応 #928104

反応方程式

5-bromo-7-azaoxindole

dimethylsulfoxide

methanol

triethylamine

Carbon monoxide

→

5-(carboethoxy)-7-azaoxindole

収率 25.7%

溶媒

ethanol

diethyl ether

反応条件

後処理

1. 1
   洗浄washed with water (10 ml)
2. 2
   抽出The aqueous layer was thoroughly extracted with diethyl ether
3. 3
   乾燥The combined organic layers were dried over anhydrous MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated under vacuum
6. 6
   その他to give crude product

実験手順

To a mixture of 5-bromo-7-azaoxindole (213 mg, 1 mmol) in dimethylsulfoxide (1 ml) and ethanol (5 ml) in Parr bomb were added triethylamine (0.31 ml, 2.25 mmol), palladium acetate (33.7 mg, 0.15 mmol), and 1,3-(bisdiphenylphosphino)propane (61.9 mg, 0.15 mmol). Carbon monoxide gas (40 atm) was applied and the reaction mixture was heated at 95° C. for 18 hours with vigorously stirring. The reaction mixture was diluted with diethyl ether (50 ml) and washed with water (10 ml). The aqueous layer was thoroughly extracted with diethyl ether. The combined organic layers were dried over anhydrous MgSO4, filtered and evaporated under vacuum to give crude product. Trituation of the crude product with methanol yielded 5-(carboethoxy)-7-azaoxindole as a tan solid (53 mg, 25.7%). 1H NMR (DMSO-d6): δ11.39 (s, 1H), 8.62 (s, 1H), 7.95 (s, 1H), 4.27 (q, 2H, J=7 Hz), 3.59 (s, 2H), 1.28 (t, 3H, J=7 Hz). MS (−ve APCI): 205 (4, M−H).

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