참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium Carbonate | HCID 10340 | — |
| 반응물 | (3,5-Dimethoxyphenyl)boronic acid | HCID 4374257 | — |
| 반응물 | 5,8-Dibromoquinoxaline | HCID 11514763 | — |
| 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 | 5-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline | HCID 59292825 | 70.7% |
반응 단계
A mixture of 3,5-dimethoxyphenylboronic acid (Step 1.8) (3.38 g, 18.6 mmol) in EtOH (15 mL) was added dropwise to a mixture of 5,8-dibromo-quinoxaline (Step 1.5) (10.7 g, 37.1 mmol, 2 equiv), PdCl2(dppf) (530 mg, 0.7 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 37 mL, 74.3 mmol, 4 equiv) in toluene (100 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 2 h, allowed to cool to rt, diluted with EtOAc and H2O, filtered through a pad of celite and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by trituration in DCM, followed by silica gel column chromatography (Hex/EtOAc, 4:1) to afford 4.54 g of the title compound as a yellow solid: ES-MS: 345.0 [M+H]+; tR=5.13 min (System 1); Rf=0.17 (Hex/EtOAc, 4:1).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08536175B2 |
|---|
| 출처 데이터셋 | uspto-grants-2013_09 |
|---|
| ORD ID | ord-0b8a36f9e64b48c9b47a8bba000f6514 |
|---|
| 출처 메모 | uspto-grants-2013_09 |
|---|
