関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | (3,5-Dimethoxyphenyl)boronic acid | HCID 4374257 | — |
| 反応物 | 5-Bromoquinoline-8-carboxylic acid | HCID 59292860 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 5-(3,5-Dimethoxy-phenyl)-quinoline-8-carboxylic acid | HCID 59292876 | 81% |
反応手順
A mixture of 3,5-dimethoxyphenylboronic acid (217 mg, 1.19 mmol, 1.2 equiv) (Step 1.8) in EtOH (0.5 mL) was added dropwise to a mixture of 5-bromo-quinoline-8-carboxylic acid (Step 159.3) (250 mg, 0.99 mmol), PdCl2(dppf) (22 mg, 0.03 mmol, 0.03 equiv), Na2CO3 (2M solution in H2O, 1 mL, 3.97 mmol, 4 equiv) in toluene (5 mL) at 105° C., under an argon atmosphere. The reaction mixture was stirred at 105° C. for 1 h, allowed to cool to rt, diluted with EtOAc and H2O, basified by addition of a 2N aqueous solution of NaOH (2 mL), filtered through a pad of celite and the filtrate was extracted with EtOAc. The aqueous layer was separated and acidified to pH 5. The resulting precipitate was collected by vacuum filtration to provide 248 mg of the title compound as a white solid: ESI-MS: 310.1 [M+H]+; tR=4.06 min (System 1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08536175B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
|---|
| ORD ID | ord-3bf40791a5b34a20b2709d8368665a72 |
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| 出典メモ | uspto-grants-2013_09 |
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