반응 #71389

반응 방정식

3,5-dimethoxyphenylboronic acid

3,6-dibromo-benzene-1,2-diamine

Na2CO3

→

title compound

수율 37.9%

4-Bromo-3′,5′-dimethoxy-biphenyl-2,3-diamine

수율 37.9%

용매

EtOAc

H2O

EtOH

toluene

반응 조건

후처리

1. 1
   온도to cool to rt
2. 2
   추출extracted with EtOAc
3. 3
   세척The organic phase was washed with H2O and brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude product was purified by silica gel column chromatography (DCM)

실험 절차

A mixture of 3,5-dimethoxyphenylboronic acid (15.1 g, 82.7 mmol, 1.1 equiv) (Step 1.8) in EtOH (50 mL) was added dropwise to a mixture of 3,6-dibromo-benzene-1,2-diamine (20 g, 75.2 mmol) (Step 1.6), PdCl2(dppf) (6.1 g, 7.5 mmol, 0.1 equiv), Na2CO3 (2 M solution in H2O, 150 mL, 300.8 mmol, 4 equiv) in toluene (300 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 3 h, allowed to cool to rt, diluted with EtOAc and H2O and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (DCM) followed by trituration in EtOH to afford 9.2 g of the title compound as a white solid: ES-MS: 323.0/325.0 [M+H]+; tR=4.43 min (System 1); Rf=0.15 (DCM).

출처