関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline | HCID 58147516 | — |
| 反応物 | 1H-Pyrazole, 1-[2-(2-methoxyethoxy)ethyl]-4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- | HCID 68631907 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | HCID 57917384 | HCID 57917384 | — |
反応手順
A mixture of 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Stage 173.1, 50 mg, 0.160 mmol), 1-[2-(2-methoxy-ethoxy)-ethyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (Stage 233.1, 47 mg, 0.160 mmol), Pd(PPh3)2Cl2 (6 mg, 0.008 mmol) and 2 M K2CO3 (216 μL, 0.432 mmol) in DME (1 mL) was stirred at 95° C. for 1 h. The mixture was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified twice by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep® silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100) to afford the title compound as a foam (tR 3.56 min (conditions 3), MH+=447.1, 1H-NMR in DMSO-d6: 8.84 (m, 1H); 8.42 (s, 1H); 8.33 (d, 1H); 8.08 (m, 2H); 8.01 (d, 1H); 7.76 (d, 1H); 7.61 (s, 1H); 7.52 (d, 1H); 7.46 (dd, 1H); 4.55 (s, 2H); 4.31 (t, 2H); 3.79 (t, 2H); 3.50 (m, 2H); 3.36 (m, 2H); 3.15 (s, 3H)).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08822468B2 |
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| 出典データセット | uspto-grants-2014_09 |
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| ORD ID | ord-31d0b4c63277414593b253b02e682408 |
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| 出典メモ | uspto-grants-2014_09 |
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