関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | Phosphorus oxychloride | HCID 24813 | — |
| 反応物 | Dichloromethane methanol ammonium hydroxide | HCID 21896990 | — |
| 反応物 | 7-Fluoro-1,5-naphthyridin-4-ol | HCID 67504324 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 8-Chloro-3-fluoro-1,5-naphthyridine | HCID 57690937 | 64.3% |
反応手順
A pressure resistant vial was charged with 7-fluoro-1,5-naphthyridin-4(1H)-one (600 mg, 3.66 mmol) and POCl3 (6.8 mL, 73.1 mmol). Vessel sealed and stirred at 110° C. for 16 hrs. Reaction mixture was cooled to room temperature and poured onto ice while stirring vigorously. While keeping reaction mixture at 0° C., it was basified to pH˜8 with 6N NaOH. Product extracted with dichloromethane. Organic layer collected, dried over sodium sulfate and concentrated to afford desired material. This was passed through a silica plug in 1-5% (90:10:1 DCM/MeOH/NH4OH)/DCM to afford 8-chloro-3-fluoro-1,5-naphthyridine (430 mg, 64% yield) as a tan solid. MS [M+H]=182.9. Calc'd for C8H4ClFN2=182.58
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08524900B2 |
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| 出典データセット | uspto-grants-2013_09 |
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| ORD ID | ord-d2769fba50d040f2a1f4cc61c0e85a31 |
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| 出典メモ | uspto-grants-2013_09 |
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