참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Pyrazole | HCID 1048 | — |
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| 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-pyrazol-1-YL)benzoic acid | HCID 53409752 | 72.8% |
반응 단계
To a mixture of 3-fluoro-2-iodobenzoic acid (1.4 g, 5.26 mmol), 1H-pyrazole (0.72 g, 10.5 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.17 mL, 1.05 mmol), CuI (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added Cs2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100° C. for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH 2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAC/DCM) to the yield the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCl3): 7.85-7.73 (m, 1H), 7.54-7.44 (m, 1H), 7.44-7.34 (m, 1H), 6.55 (s, 1H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09062044B2 |
|---|
| 출처 데이터셋 | uspto-grants-2015_06 |
|---|
| ORD ID | ord-4a37681f5b8242f9a0c23fb910f94597 |
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| 출처 메모 | uspto-grants-2015_06 |
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