참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Picolinic acid | HCID 1018 | — |
| 반응물 | Diethyl Malonate | HCID 7761 | — |
| 반응물 | Cesium carbonate | HCID 10796 | — |
| 반응물 | 5-Bromo-2-iodopyridine | HCID 593690 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | Diethyl 2-(5-bromopyridin-2-yl)malonate | HCID 59238270 | 50% |
반응 단계
A mixture of 5-bromo-2-iodo-pyridine (56.8 g, 0.2 mol), malonic acid diethyl ester (64 g, 0.4 mol), CuI (3.8 g, 0.02 mol), Cs2CO3 (195.5 g, 0.6 mol) and pyridine-2-carboxylic acid (2.46 g, 0.04 mol) in 1,4-dioxane (400 mL) was stirred at 70 degrees Celsius under N2 for 24 hours. After cooling to room temperature, the solid was filtered and the solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and washed with water, brine, dried over Na2SO4, filtered, concentrated in vacuo, the crude product was purified by flash chromatography (Petroleum Ether:EtOAc=20:1) to obtain an oil (31.6 g, 50%). MS: calc'd 316 (MH+), exp 316 (MH+). 1H NMR (d6-DMSO, 400 MHz), 8.68 (d, 1H, J=2.4 Hz), 8.11 (dd, 1H, J=2.4, 8.4 Hz), 7.45 (d, 1H, J=8.4 Hz), 5.16 (s, 1H), 4.20-4.07 (m, 4H), 1.18 (t, J=8.4 Hz, 6H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08202866B2 |
|---|
| 출처 데이터셋 | uspto-grants-2012_06 |
|---|
| ORD ID | ord-a0f0e68cae3740dab0a1c7d2c66551dc |
|---|
| 출처 메모 | uspto-grants-2012_06 |
|---|
