참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | Phosphorus oxychloride | HCID 24813 | — |
| 반응물 | Dichloromethane methanol ammonium hydroxide | HCID 21896990 | — |
| 반응물 | 7-Fluoro-1,5-naphthyridin-4-ol | HCID 67504324 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 생성물 | 8-Chloro-3-fluoro-1,5-naphthyridine | HCID 57690937 | 64.3% |
반응 단계
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
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US08524900B2 |
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| 출처 데이터셋 | uspto-grants-2013_09 |
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| ORD ID | ord-d2769fba50d040f2a1f4cc61c0e85a31 |
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| 출처 메모 | uspto-grants-2013_09 |
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