참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | 4-Bromo-6-(trifluoromethyl)-1H-indazole | HCID 24729232 | — |
| 반응물 | 4-(2-Hydroxyethylcarbamoyl)benzeneboronic acid | HCID 44119359 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | Trifluoroacetic acid | HCID 6422 | — |
| 생성물 | HCID 89783055 | HCID 89783055 | 30% |
반응 단계
A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.300 g, 1.132 mmol), (4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid (0.237 g, 1.132 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 4.5 minutes. The product-containing fractions were combined and volatiles removed in vacuo to give a TFA salt of the title compound as white solid (0.12 g, 30%). 1H NMR (400 MHz, CD3OD) δ ppm 3.56 (t, J=5.81 Hz, 2H), 3.75 (t, J=5.81 Hz, 2H), 7.49 (d, J=1.01 Hz, 1H), 7.78-7.89 (m, 2H), 7.93 (s, 1H), 8.00-8.10 (m, 2H), 8.21-8.32 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C17H14F3N3O2, 350.1. found 350.1.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09434743B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_09 |
|---|
| ORD ID | ord-499578f0ade742d8a598a93cc082bdb9 |
|---|
| 출처 메모 | uspto-grants-2016_09 |
|---|
