関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | tert-Butyl acrylate | HCID 15458 | — |
| 反応物 | Tri-o-tolylphosphine | HCID 80271 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Methyl 2-((5-bromopyridin-2-yl)amino)acetate | HCID 22139049 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Propionitrile | HCID 7854 | — |
| 生成物 | tert-butyl (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]acrylate | HCID 66905699 | 93.3% |
反応手順
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).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07741339B2 |
|---|
| 出典データセット | uspto-grants-2010_06 |
|---|
| ORD ID | ord-765f834566c84bcfa82e57d0ee0a57e4 |
|---|
| 出典メモ | uspto-grants-2010_06 |
|---|
