참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 2-Acetamidopyridine-5-boronic acid pinacol ester | HCID 17750202 | — |
| 반응물 | 9-Chloro-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene | HCID 57900309 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | Acetonitrile--water (1/1) | HCID 18373917 | — |
| 생성물 | HCID 58204039 | HCID 58204039 | 15% |
반응 단계
9-Chloro-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene (416 mg, 1.0 mmol), N-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-acetamide (314 mg, 1.2 mmol), Cs2CO3 (650 mg, 2.0 mmol), Pd(dppf)Cl2 (73 mg, 0.10 mmol) and CH3CN—H2O (1:1, 4 mL) were added in a 10 mL of sealed tube, and the mixture was heated by microwave at 120° C. for 20 min under N2. The reaction mixture was filtered to gather the solution and water was added. The mixture was extracted by DCM (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated in vacuo, and purified by preparative HPLC to 247 (77 mg, yield: 15%). 1HNMR (DMSO-d6, 400 MHz): δ10.62 (s, 1H), 8.88 (s, 1H), 8.27 (s, 1H), 8.15 (s, 2H), 7.42 (t, J=0.8 Hz, 1H), 7.89-7.81 (m, 3H), 7.47 (t, J=8.8 Hz, 2H), 7.15 (s, 1H), 4.27 (s, 2H), 3.17 (s, 2H), 2.08 (s, 3H). ESI-MS: m/z=517 [M+H+]
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US09175009B2 |
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| 출처 데이터셋 | uspto-grants-2015_11 |
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| ORD ID | ord-81c2ac698ffe4bdaad7461cd0ccf66fa |
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| 출처 메모 | uspto-grants-2015_11 |
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