참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium Carbonate | HCID 10340 | — |
| 반응물 | (3,5-Dimethoxyphenyl)boronic acid | HCID 4374257 | — |
| 반응물 | 3,6-Dibromobenzene-1,2-diamine | HCID 11821532 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | Ethanol | HCID 702 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Toluene | HCID 1140 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | 4-Bromo-3',5'-dimethoxy-biphenyl-2,3-diamine | HCID 59292878 | 37.9% |
반응 단계
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 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08536175B2 |
|---|
| 출처 데이터셋 | uspto-grants-2013_09 |
|---|
| ORD ID | ord-99b0390f550b43afa7312b65ce2d7fbd |
|---|
| 출처 메모 | uspto-grants-2013_09 |
|---|
