関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 4-Carboxyphenylboronic Acid | HCID 312183 | — |
| 反応物 | 6-Trifluoromethylsulfonyloxy-8-methoxy-1,7-naphthyridine | HCID 23284635 | — |
| 触媒 | Tri-o-tolylphosphine | HCID 80271 | — |
| 触媒 | 1,5-Diphenylpenta-1,4-dien-3-one;palladium | HCID 154270 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 6-(4-Carboxyphenyl)-8-methoxy-1,7-naphthyridine | HCID 23284642 | 80.8% |
反応手順
To a solution of 6-trifluoromethylsulfonyloxy-8-methoxy-1,7-napthyridine (1.5 g, 4.86 mmol) in DMF (40 ml) is added 4-carboxy-phenylboronic acid (0.866 g, 5.34 mmol), bis(dibenzylidenacetone) palladium (112 mg, 0.167 mmol), tri-o-tolylphosphine (96 mg, 0.32 mmol) and aqueous Na2CO3 (14.6 ml, 2N,). The reaction mixture is stirred at 110° for 3 h. The hot solution is filtred through cellit and the solution evaporated to dryness. The crude product is dissolved in hot water (60 ml) and the water phase washed with ethyl acetate (3×50 ml). The product is precipitated from the water phase by carefully adding aqueous HCl (2N, 6 ml). The suspension is filtered and the crude product is stirred again in hot ethyl acetate (50 ml). The cold suspension is filtered to yield the title compound (1.10 g). M+280; Melting point >300°.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06136821 |
|---|
| 出典データセット | uspto-grants-2000_10 |
|---|
| ORD ID | ord-449fc1ba55304cbb90163e63a52ba620 |
|---|
| 出典メモ | uspto-grants-2000_10 |
|---|