関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | B-(1E)-1-Hexenylboronic acid | HCID 5326225 | — |
| 反応物 | 3-(4-Bromo-1,2-oxazol-3-yl)pyridine | HCID 57548041 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 触媒 | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 3-(4-Hex-1-enyl-isoxazol-3-yl)-pyridine | HCID 67285366 | 72.5% |
反応手順
To anhydrous THF (30 ml) containing compound 64 (0.64 g, 2.84 mmol), were added 1.5 eq of (E)-hexene-1-ylboronic acid (0.55 g). The resulting mixture was stirred for 2 hours under N2. Successively were added 2 eq of K3PO4 (1.2 g), 2 mol % of Pd(OAc)2 (13 mg) and 4 mol % of S-Phos (47 mg). After the addition, the resulting solution was warmed at 65° C. for 18 hours under N2. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether/PE 1/1) to afford 3-(4-hex-1-enyl-isoxazol-3-yl)-pyridine (compound 67A) as an oil (0.47 g, 69%). 1H-NMR (400 MHz, CDCl3): δ 8.9 (d, J=2 Hz, 1H), 8.72 (dd, J=5 Hz, 2 Hz, 1H), 8.49 (s, 1H), 8.0 (dt, J=8 Hz, 2 Hz, 1H), 7.45-7.41 (m, 1H), 6.11-5.99 (m, 2H), 2.22-2.14 (m, 2H), 1.46-1.29 (m, 4H), 0.91 (t, J=7 Hz, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08586606B2 |
|---|
| 出典データセット | uspto-grants-2013_11 |
|---|
| ORD ID | ord-bb0a408f2b2a4996a0d3e37675a74b49 |
|---|
| 出典メモ | uspto-grants-2013_11 |
|---|
