반응 #46451

반응 방정식

3-benzoyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester

NaBH3CN

EtOAc H2O

→

3-benzyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester

수율 30.1%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   세척washed with water and brine
3. 3
   건조After drying over MgSO4
4. 4
   농축the organic fraction was concentrated in vacuo
5. 5
   기타the resulting residue was purified by flash chromatography

실험 절차

To a solution of 3-benzoyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester (2.4 g, 6.45 mmol) in 1,2-dichloroethane (80 ml) was added NaBH3CN (3.24 g, 51.6 mmol) and ZnI2 (6.18 g, 19.4 mmol). After stirring at room temperature for 30 minutes, the reaction mixture was poured into a mixture of EtOAc/H2O. The organic layer was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting residue was purified by flash chromatography to give 3-benzyl-7-bromo-1H-indole-2-carboxylic acid ethyl ester as yellow solid (696 mg, 30%). 1H NMR (CDCl3, 300 MHz) δ: 1.39 (t, 3H, J=7.13 Hz), 4.43 (q, 2H, J=7.13 Hz), 4.49 (s, 2H), 6.98 (t, 1H, J=7.8 Hz), 7.22 (m, 5H), 7.46 (d, 1H, J=7.60 Hz), 7.54 (d, 1H, J=8.10 Hz).

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