반응 #339780

반응 방정식

LDA

4-iodoaniline

K2CO3

→

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

수율 124.8%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONafter the addition
2. 2
   기타slowly brought to room temperature
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   온도It is then cooled at −78° C.
5. 5
   기타is brought to room temperature
6. 6
   workup.STIRRINGstirred overnight
7. 7
   기타The precipitate is collected
8. 8
   세척washed with water
9. 9
   기타after drying
10. 10
    기타is chromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

실험 절차

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%).

출처