反应详情

A mixture of 1-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile (1.25 g, 3.83 mmol), 4-(4,4,5,5-tetramethyl)-1,3-2-dioxaboralanyl-2-yl-aniline (0.96 g, 4.90 mmol), CsF (1.46 g, 9.58 mmol) and Pd(PPh3)2Cl2 (110 mg, 0.15 mmol) in DME (20 mL) is added to a flask and alternatively evacuated and flushed with N2. The reaction is then heated at reflux for 24 h and then cooled to room temperature. The reaction mixture is diluted with H2O and extracted with EtOAc (2×). The combined organic phases are washed with H2O and saturated NaCl and then dried over MgSO4 and concentrated. The crude reaction mix is purified by flash chromatography on silica gel using EtOAc/CH2Cl2 (5/95) as eluent to afford 765 mg (69%) of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile as a yellow solid.

1. additionis added to a flask
2. customalternatively evacuated
3. customflushed with N2
4. temperatureThe reaction is then heated
5. temperatureat reflux for 24 h
6. additionThe reaction mixture is diluted with H2O
7. extractionextracted with EtOAc (2×)
8. washThe combined organic phases are washed with H2O and saturated NaCl
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customThe crude reaction
12. additionmix
13. customis purified by flash chromatography on silica gel