Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
1-Fluoro-3-iodobenzene → 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 1-Fluoro-3-iodobenzene | HCID 70725 | — |
| 반응물 | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| 반응물 | Ethyl 5-((trimethylsilyl)ethynyl)nicotinate | HCID 67047749 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178419050 | HCID 178419050 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester | HCID 67047762 | 80% |
반응 단계
Add a 1 M solution of tetrabutylammonium fluoride (0.88 g, 3.38 mmol) in tetrahydrofuran to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester, (prepared as described in PREPARATION 16), (0.84 g, 3.38 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −78° C. Warm to room temperature, stir overnight and then dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 mg, 80%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07915424B2 |
| 출처 데이터셋 | uspto-grants-2011_03 |
| ORD ID | ord-1237bf71b2dd440cace619e612230c93 |
| 출처 메모 | uspto-grants-2011_03 |