참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 1H-1,2,3-Triazole | HCID 67516 | — |
| 반응물 | (1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine | HCID 11275066 | — |
| 반응물 | 3-Fluoro-2-iodobenzoic acid | HCID 22320308 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | 3-fluoro-2-(1H-1,2,3-triazol-1-yl)benzoic acid | HCID 67087111 | — |
반응 단계
To 3-fluoro-2-iodobenzoic acid (4.5 g, 16.9 mmol) dissolved in dioxane (33.8 mL) and H2O (0.09 mL) was added Cs2CO3 (11.02 g, 33.8 mmol), CuI (161 mg, 0.85 mmol), 2H-1,2,3-triazole (1.96 mL, 33.8 mmol), and trans-N,N-dimethyl-1,2-cyclohexanediamine (0.53 mL, 3.38 mmol). The mixture was then heated to 100° C. overnight, cooled to room temperature, diluted with H2O, and extracted with EtOAc. The aqueous layer was then acidified and extracted with EtOAc. The combined organics were dried and concentrated. From this concentrate a solid precipitated to provide intermediate A-33 (285 mg, 8%). MS (ESI) mass calcd for C9H6FN3O2, 207.0. m/z found 208.1 [M+H]+. 1H NMR (500 MHz, Methanol-d4) δ 6.81-6.77 (m, 1H), 6.46-6.40 (m, 2H), 6.30-6.23 (m, 1H), 6.18-6.12 (m, 1H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US09447117B2 |
|---|
| 출처 데이터셋 | uspto-grants-2016_09 |
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| ORD ID | ord-4dea00b4ab2f43b8ac28fd28e2f79abf |
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| 출처 메모 | uspto-grants-2016_09 |
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