참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | 3,5-Dichloro-2-cyanopyridine | HCID 2769699 | — |
| 반응물 | Ethyl 4-ethynylbenzoate | HCID 15540683 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | Ammonium Hydroxide | HCID 14923 | — |
| 생성물 | Ethyl 4-((5-chloro-6-cyanopyridin-3-yl)ethynyl)benzoate | HCID 66874947 | — |
반응 단계
A solution of 3,5-dichloropicolinonitrile (commercially available) (1.0 eq.), ethyl 4-ethynylbenzoate (commercially available) (1.0 eq.), trans-dichlororbis(triphenylphosphine)palladium (II) (10 mol %), copper (I) iodide (20 mol %), and triethylamine (5.0 eq.) in DMF (0.3 M) was stirred at 50° C. for 3 hours. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate and 10% aqueous ammonium hydroxide. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% ethyl acetate in hexane to give ethyl 4-((5-chloro-6-cyanopyridin-3-yl)ethynyl)benzoate as a white solid.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08895577B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_11 |
|---|
| ORD ID | ord-f4eee001da0649dfbaa8d9088bfba086 |
|---|
| 출처 메모 | uspto-grants-2014_11 |
|---|
