関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-Carboxyphenylboronic Acid | HCID 312183 | — |
| 反応物 | 3-Chloro-7-methoxy-4-methylisoquinoline | HCID 86698074 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Degme H2O | HCID 49835946 | — |
| 生成物 | 4-(7-Methoxy-4-methylisoquinolin-3-yl)benzoic acid | HCID 67974891 | 13% |
反応手順
To a mixture of 3-chloro-7-methoxy-4-methylisoquinoline (Intermediate 15) (470 mg, 2.27 mmol), 4-carboxyphenylboronic acid (451 mg, 2.72 mmol) and K2CO3 (627 mg, 4.54 mmol) in DEGME/H2O (7 mL/1 mL) was added Pd(dppf)Cl2 (40.8 mg, 0.050 mmol) under N2 atmosphere. Then the mixture was heated to 120° C. for 16 hours. H2O (30 mL) was added, and the resulting mixture was extracted with EtOAc (15 mL×2). The aqueous layer was neutralized with 1N aqueous HCl to pH=7, extracted with EtOAc (20 mL×3). The combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated. Purification by silica gel column (PE/EtOAc=20/1 to 1/1, then EtOAc) gave 4-(7-methoxy-4-methylisoquinolin-3-yl)benzoic acid (85.0 mg, yield 13%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09012646B2 |
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| 出典データセット | uspto-grants-2015_04 |
|---|
| ORD ID | ord-2c8ae20877284d7d8e763803ed63b51f |
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| 出典メモ | uspto-grants-2015_04 |
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