참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 1,4-Dioxane | HCID 31275 | — |
| 반응물 | 1-Methyl-5-(tributylstannyl)-1H-pyrazole | HCID 21867455 | — |
| 반응물 | Methyl 2-amino-4-ethyl-5-iodobenzoate | HCID 53424411 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | 2-amino-4-ethyl-5-(2-methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester | HCID 59164471 | 68.3% |
반응 단계
2-Amino-5-iodo-4-ethyl-benzoic acid methyl ester (280 mg, 0.92 mmol) and 1-methyl-5-tributylstannanyl-1H-pyrazole (409 mg, 1.2 equiv) were weighed in air and added to a flame-dried flask. [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (75 mg, 0.1 equiv) was added and the flask was closed by a septum. Dioxane (1 mL) was added and the mixture was stirred at 100° C. for 18 h (TLC control). The mixture was dissolved with EtOAc, filtered and evaporated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6)) to yield 2-amino-4-ethyl-5-(2-methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester (163 mg, 68% yield) as a yellow solid. ESI-MS: m/z 260.3 [M+H]+, rt 6.37 min.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08513268B2 |
|---|
| 출처 데이터셋 | uspto-grants-2013_08 |
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| ORD ID | ord-e94d67e4ce974727801ad8d48b6dfecc |
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| 출처 메모 | uspto-grants-2013_08 |
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