Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
HRID 919913생성일: 2026년 10월 25일
Hydrochloric Acid → 3-Benzo[1,2,5]oxadiazol-5-yl-1-benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester
https://huagongshe.com/reaction/919913
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Water | HCID 962 | — |
| 반응물 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 반응물 | Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid | HCID 4672597 | — |
| 반응물 | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| 반응물 | 1-Benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester | HCID 68297477 | — |
| 촉매 | palladium(II) acetate | HCID 167845 | — |
| 용매 | Toluene | HCID 1140 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | Sodium chloride; water | HCID 57417360 | — |
| 생성물 | 3-Benzo[1,2,5]oxadiazol-5-yl-1-benzyl-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester | HCID 136377240 | 36.7% |
반응 단계
A mixture of 1-benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (80 mg, 0.21 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (51 mg, 0.31 mmol), K3PO4 (87 mg, 0.41 mmol), H2O (7.4 mg, 0.41 mmol), SPhos (4.2 mg, 0.010 mmol) and Pd(OAc)2 (4.2 mg, 0.0062 mmol) in toluene (5 mL) was heated at 100° C. under nitrogen atmosphere for 16 h. After the mixture was cooled to r.t., brine and EtOAc were added. 1 M HCl was added with stirring until pH was about 3, and the organic layer was dried over MgSO4 and concentrated. The crude product was first purified by silica gel chromatography (0-60% EtOAc/hexanes+1% AcOH), then by preparative TLC (20% EtOAc/CH2Cl2) to give 33 mg of the title compound. MS: (+) m/z 429.27 (M+1).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US09271970B2 |
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| 출처 데이터셋 | uspto-grants-2016_03 |
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| ORD ID | ord-b8ab95a9b5004163b191976db4a9fab9 |
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| 출처 메모 | uspto-grants-2016_03 |
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