참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Trifluoroacetic acid | HCID 6422 | — |
| 반응물 | Potassium Carbonate | HCID 11430 | — |
| 반응물 | Iodobenzene | HCID 11575 | — |
| 반응물 | 1-[2-(2-propynyloxy)ethyl)-1H-imidazo[4,5-c]quinolin-4-amine | HCID 9856610 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178418476 | HCID 178418476 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Acetonitrile--water (1/1) | HCID 18373917 | — |
| 생성물 | HCID 12114211 | HCID 12114211 | 21% |
반응 단계
Under a nitrogen atmosphere, a mixture of 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (10 g, 37.6 mmol), anhydrous N,N-dimethylformamide (150 mL) and potassium carbonate (6.23 g, 45.1 mmol) was heated to 70° C. Iodobenzene (4.43 mL, 39.5 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.53 g, 0.75 mol), and copper(I) iodide (0.29 g, 1.50 mmol) were added and the mixture was allowed to stir for 0.5 hour. The temperature was raised to about 85° C. After 1.5 hours analysis by HPLC (reverse phase, acetonitrile/water with 0.1% trifluoroacetic acid) indicated that the reaction was complete. The mixture was allowed to cool to ambient temperature and then it was filtered. The filtrate was concentrated under reduced pressure. The residue was purified twice by flash chromatography (95/5 dichloromethane/methanol) to provide 2.7 g of 1-{2-[(3-phenyl-2-propynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 196-197° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US06953804B2 |
|---|
| 출처 데이터셋 | uspto-grants-2005_10 |
|---|
| ORD ID | ord-85bcc2f639e241319376e689818f45d5 |
|---|
| 출처 메모 | uspto-grants-2005_10 |
|---|
