참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | 4-Iodo-1,2-dimethylbenzene | HCID 141646 | — |
| 반응물 | 5-Ethynylnicotinonitrile | HCID 22416563 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178419050 | HCID 178419050 | — |
| 용매 | Diethyl Ether | HCID 3283 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 생성물 | 5-(3,4-Dimethylphenylethynyl)-nicotinonitrile | HCID 67047542 | 62% |
반응 단계
Combine 4-iodo-o-xylene (0.362 g, 1.561 mmol), bis(triphenylphosphine)palladium (II) dichloride (55 mg, 0.078 mmol), and copper (I) iodide (30 mg, 0.156 mmol) in triethylamine (0.653 mL, 4.683 mmol) and stir under nitrogen for 5 min at 80° C. Add a solution of 5-ethynylnicotinonitrile, (prepared essentially as described in PREPARATION 4), (200 mg, 1.561 mmol) in anhydrous acetonitrile (2.50 mL), and stir under nitrogen overnight. Cool to room temperature and dilute with diethyl ether. Wash with a saturated aqueous solution of sodium bicarbonate, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 95:5 to 50:50 dichloromethane:ethyl acetate, to give the title compound as a yellow solid (225 mg, 62%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07915424B2 |
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| 출처 데이터셋 | uspto-grants-2011_03 |
|---|
| ORD ID | ord-f070616815b445c8816ea82e3b9c3f6a |
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| 출처 메모 | uspto-grants-2011_03 |
|---|
