反応 #339780

反応方程式

LDA

4-iodoaniline

K2CO3

→

2-(4-aminophenyl)-1-cyclopropyl-6-methoxyindole-3-carbonitrile

収率 124.8%

溶媒

DMF

反応条件

後処理

1. 1
   workup.ADDITIONafter the addition
2. 2
   その他slowly brought to room temperature
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   温度It is then cooled at −78° C.
5. 5
   その他is brought to room temperature
6. 6
   workup.STIRRINGstirred overnight
7. 7
   その他The precipitate is collected
8. 8
   洗浄washed with water
9. 9
   その他after drying
10. 10
    その他is chromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

実験手順

To a solution of the intermediate (2.65 g, 12.5 mmol) obtained above and triisopropyl borate (3.38 g, 4.14 mL, 18.8 mmol) in dry THF (18 mL) at −78° C. is added LDA (10 mL, 1.5 M, 15.0 mmol). The mixture is stirred at −78° C. for 15 min after the addition, then slowly brought to room temperature and stirred for 30 min. It is then cooled at −78° C. and followed by the addition of 4-iodoaniline (3.29 g, 15.0 mmol), PdCl2(dppf) (0.46 g, 0.6 mmol), DMF (40 mL) and K2CO3 (18.8 mL, 2.0 M, 37.6 mmol). The mixture is brought to room temperature slowly and stirred overnight and then poured into ice-water (400 mL). The precipitate is collected and washed with water, and after drying, is chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to furnish 2-(4-aminophenyl)-1-cyclopropyl-6-methoxyindole-3-carbonitrile (2.84 g, 75%).

出典