참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | 2-Fluoro-4-iodobenzonitrile | HCID 2774518 | — |
| 반응물 | 4,7-Dimethoxy-1,10-phenanthroline | HCID 10462298 | — |
| 반응물 | Gimeracil | HCID 54679224 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Dimethyl Sulfoxide | HCID 679 | — |
| 용매 | Water | HCID 962 | — |
| 생성물 | 4-(5-chloro-4-hydroxy-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrile | HCID 67366532 | 74.7% |
반응 단계
A mixture of 2-fluoro-4-iodobenzonitrile (4000 mg, 16.19 mmol), 5-chloro-4-hydroxypyridin-2(1H)-one (2357 mg, 16.19 mmol), 4,7-dimethoxy-1,10-phenanthroline (778 mg, 3.24 mmol), copper(I) iodide (617 mg, 3.24 mmol) and potassium carbonate (4476 mg, 32 4 mmol) in DMSO (40 mL) was stirred at 140° C. under N2 for 3 h. After cooled to rt, the reaction mixture was diluted with H2O (50 mL) and added 1N HCl to adjust the pH to ˜2 (pH paper). The resulting mixture was extracted with EtOAc (400 mL, 2×). The combined extracts were dried (Na2SO4) and evaporated under reduced pressure to give black oil. The residue was purified by flash chromatography (SiO2, 0 to 7% MeOH/CH2Cl2) to give brown oil (3.2 g, 43.3%). MS (ESI) 265 (M+H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08232404B2 |
|---|
| 출처 데이터셋 | uspto-grants-2012_07 |
|---|
| ORD ID | ord-da7e54358e6340fdbb492fc3fbd4f529 |
|---|
| 출처 메모 | uspto-grants-2012_07 |
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