참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 5-bromo-1H-indazole | HCID 761929 | — |
| 반응물 | (Prop-1-en-2-yl)boronic acid | HCID 10855372 | — |
| 촉매 | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| 촉매 | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 1H-Indazole | HCID 9221 | 298.8% |
| 생성물 | 5-(prop-1-en-2-yl)-1H-indazole | HCID 86678017 | — |
반응 단계
A mixture of prop-1-en-2-ylboronic acid (1.2 g), 5-bromo-1H-indazole (1.0 g, 5.1 mmol), Pd(dba)2 (0.04 g, 0.07 mmol), X-phos (0.04 g, 0.08 mmol) and Cs2CO3 (3.0 g, 9.2 mmol) in a mixture of 30 mL of DMF and 5 mL of water was stirred at 130° C. under nitrogen for 8 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (200-300 mesh, eluting with a mixture of ethyl acetate and petroleum ether (1:5, v/v) to give a 2:3 mixture 5-(prop-1-en-2-yl)-1H-indazole and 1H-indazole (0.9 g). The crude mixture was used into the next step without further purification. LCMS: (M+H)+=159; 1H NMR (300 MHz, DMSO): δ 8.08 (s, 1H), 7.81-7.80 (m, 1H), 7.62 (dd, 1H, J1=8.7 Hz, J2=1.5 Hz), 7.53-7.46 (m, 1H), 5.40-5.39 (m, 1H), 5.12-5.11 (m, 1H), 2.24 (s, 3H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08658646B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_02 |
|---|
| ORD ID | ord-2ec8a53a03974763972286cc2b7cca37 |
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| 출처 메모 | uspto-grants-2014_02 |
|---|
