تفاعل #339671

معادلة التفاعل

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

CsF

→

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

المردود 137.1%

المذيبات

DME

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added to a flask
2. 2
   أخرىalternatively evacuated
3. 3
   أخرىflushed with N2
4. 4
   درجة الحرارةThe reaction is then heated
5. 5
   درجة الحرارةat reflux for 24 h
6. 6
   workup.ADDITIONThe reaction mixture is diluted with H2O
7. 7
   استخلاصextracted with EtOAc (2×)
8. 8
   غسيلThe combined organic phases are washed with H2O and saturated NaCl
9. 9
   تجفيفdried over MgSO4
10. 10
    تركيزconcentrated
11. 11
    أخرىThe crude reaction
12. 12
    workup.ADDITIONmix
13. 13
    أخرىis purified by flash chromatography on silica gel

الإجراء التجريبي

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.

المصدر