Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Triethylamine → 5-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Triethylamine | HCID 8471 | — |
| 반응물 | Methyl 5-bromothiophene-2-carboxylate | HCID 605713 | — |
| 반응물 | N-(Prop-2-yn-1-yl)methanesulfonamide | HCID 14025440 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | HCID 178418397 | HCID 178418397 | — |
| 용매 | Acetonitrile | HCID 6342 | — |
| 생성물 | 5-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester | HCID 53752688 | 50.3% |
반응 단계
To a solution of 5-bromo-thiophene-2-carboxylic acid methyl ester (1.66 g, 8.0 mmol), N-prop-2-ynyl-methanesulfonamide (1.09 g, 8.2 mmol), Et3N (1.7 mL, 12.1 mmol), and CH3CN (30 mL) was added Pd(PPh3)4 (462 mg, 0.4 mmol) followed by CuI (76 mg, 0.4 mmol). The reaction was heated at reflux for 24 h and was cooled to room temperature. The volatiles were removed in vacuo and the residue was purified via flash chromatography (20% EtOAc in hexanes to 33% EtOAc in hexanes) to yield 5-(3-methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester as a pale yellow solid (1.1 g). 1H NMR (300 MHz, CDCl3) δ 7.64 (d, 1H), 7.14 (d, 1H), 4.60 (m, 1H), 4.22 (d, 2H), 3.88 (s, 3H), 3.10 (s, 3H); MS 274 (M+1).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06649657B2 |
| 출처 데이터셋 | uspto-grants-2003_11 |
| ORD ID | ord-748b89c385eb487ba195abd096babfd2 |
| 출처 메모 | uspto-grants-2003_11 |