참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | tert-Butyl acrylate | HCID 15458 | — |
| 반응물 | Tri-o-tolylphosphine | HCID 80271 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | Methyl 2-((5-bromopyridin-2-yl)amino)acetate | HCID 22139049 | — |
| 촉매 | palladium(II) acetate | HCID 167845 | — |
| 용매 | Propionitrile | HCID 7854 | — |
| 생성물 | tert-butyl (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]acrylate | HCID 66905699 | 93.3% |
반응 단계
A solution of 5-bromo-2-(methoxycarbonylmethyl)aminopyridine (4.69 g, 19.1 mmole, from Preparation 28 (c)), tert-butyl acrylate (11.2 mL, 76.5 mmole), DIEA (6.7 mL, 38.5 mmole), Pd(OAc)2 (215 mg, 1 mmole), and P(o-tol)3 (583 mg, 2 mmole) in propionitrile (100 mL) was purged with Ar, then was heated at reflux. After 18 h, the reaction was allowed to cool to room temperature then was concentrated to dryness. The residue was purified by flash chromatography on silica gel (40% EtOAc/hexane) to give the title compound (5.21 g, 93%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.19 (s, 1 H), 7.62 (dd, 1 H), 7.47 (d, J=16.0 Hz, 1 H), 6.48 (d, J=8.7 Hz, 1 H), 6.17 (d, J=15.9 Hz, 1 H), 5.21 (br s, 1 H), 4.20 (d, J=5.4 Hz, 2 H), 3.79 (s, 3 H), 1.52 (s, 1 H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07741339B2 |
|---|
| 출처 데이터셋 | uspto-grants-2010_06 |
|---|
| ORD ID | ord-765f834566c84bcfa82e57d0ee0a57e4 |
|---|
| 출처 메모 | uspto-grants-2010_06 |
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