참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 반응물 | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| 반응물 | 5-Chloro-2,3-difluoropyridine | HCID 2783248 | — |
| 반응물 | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| 촉매 | palladium(II) acetate | HCID 167845 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | 2,3-difluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridine | HCID 57691365 | 88.5% |
반응 단계
A sealable flask was charged with 5-chloro-2,3-difluoropyridine (1.541 g, 10.3 mmol), palladium(ii) acetate (0.116 g, 0.515 mmol), potassium phosphate tribasic (6.56 g, 30.9 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.57 g, 12.4 mmol), and X-Phos (0.491 g, 1.03 mmol). The flask was sealed with a septum cap, then dioxane (20 mL) and H2O (2 mL) were added. The resulting mixture was sparged with N2 for 10 min, and then heated at 100° C. for 2 h. The solution was cooled to rt and then concentrated and purified by flash chromatography using eluent 99:1 Hexanes:EtOAc to 60:40 Hexanes:EtOAc gradient to afford 2,3-difluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridine (1.78 g, 88.5% yield) as a colorless film. LRMS (ESI) m/z calcd for C9H7F2N3 (M+H) 197.1. found 197.4.
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-d9fac620b91544978d069c4c72220021 |
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| 출처 메모 | uspto-grants-2013_09 |
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