関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 4-Carboxyphenylboronic Acid | HCID 312183 | — |
| 反応物 | Trifluoro-methanesulfonic acid 8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl ester | HCID 10571743 | — |
| 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-(3-cyanophenyl)-1,7-naphthyridine | HCID 9928390 | 56.2% |
反応手順
To a solution of 6-trifluoromethylsulfonyloxy-8-(3-cyanophenyl)-1,7-napthyridine (2.15 g, 5.67 mmol) in DMF (21.5 ml) is added 4-carboxy-phenylboronic acid (1.13 g, 6.81 mmol), bis(dibenzylidenacetone) palladium (131 mg, 0.23 mmol), triphenylphosphine (95 mg, 0.36 mmol) and aqueous K2CO3 (2N, 17 ml). The reaction mixture is stirred at 80° for 2.5 h. The hot solution is filtered through cellit and the crude product is precipitated by carefully adding water (10 ml) and aqueous HCl (2N, 8 ml). The suspension is filtered and the crude product is stirred in hot THF (30 ml). The cold suspension is filtered again to yield the title compound (1.12 g). M+H=352. Melting point >300°. Retention time HPLC=7.58 min (column: LiChroCart 125-4, Supersphere 60 RP-select B, 400; eluent: acetonitrile-water (0.1% TFA)=45:55; 1 ml/min; detection at 254 nm).
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-3fd7c358944347ac925b015aa64e3bf0 |
|---|
| 出典メモ | uspto-grants-2000_10 |
|---|
