تفاعل #339780

معادلة التفاعل

LDA

4-iodoaniline

K2CO3

→

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

المردود 124.8%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONafter the addition
2. 2
   أخرىslowly brought to room temperature
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   درجة الحرارةIt is then cooled at −78° C.
5. 5
   أخرىis brought to room temperature
6. 6
   workup.STIRRINGstirred overnight
7. 7
   أخرىThe precipitate is collected
8. 8
   غسيلwashed with water
9. 9
   أخرىafter drying
10. 10
    أخرىis chromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

الإجراء التجريبي

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%).

المصدر