참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Tetrahydrofuran | HCID 8028 | — |
| 반응물 | Ammonium Chloride | HCID 25517 | — |
| 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 | 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 in tetrahydrofuran (0.88 g, 3.38 mmol) to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester (0.84 g, 3.38 mmol), (prepared essentially as described in PREPARATION 16), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −780C. Warm to room temperature, stir overnight and dilute the mixture with ethyl acetate and an aqueous saturated solution of ammonium chloride. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting 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 g, 80%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07915424B2 |
|---|
| 출처 데이터셋 | uspto-grants-2011_03 |
|---|
| ORD ID | ord-a0fe3f254a904a1c9d2c2616b051a16f |
|---|
| 출처 메모 | uspto-grants-2011_03 |
|---|
