반응 #339671

반응 방정식

1-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile

CsF

→

2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

수율 137.1%

용매

DME

반응 조건

후처리

1. 1
   workup.ADDITIONis added to a flask
2. 2
   기타alternatively evacuated
3. 3
   기타flushed with N2
4. 4
   온도The reaction is then heated
5. 5
   온도at reflux for 24 h
6. 6
   workup.ADDITIONThe reaction mixture is diluted with H2O
7. 7
   추출extracted with EtOAc (2×)
8. 8
   세척The combined organic phases are washed with H2O and saturated NaCl
9. 9
   건조dried over MgSO4
10. 10
    농축concentrated
11. 11
    기타The crude reaction
12. 12
    workup.ADDITIONmix
13. 13
    기타is purified by flash chromatography on silica gel

실험 절차

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.

출처