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4-(Hydroxymethyl)benzeneboronic acid → 3-Amino-4-(hydroxymethylphenyl)-6-bromophthalimide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-(Hydroxymethyl)benzeneboronic acid | HCID 2734706 | — |
| 反応物 | 3-Amino-4-iodo-6-bromophthalimide | HCID 68488717 | — |
| 触媒 | Cuprous 2-thiophenecarboxylate | HCID 11194830 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-Amino-4-(hydroxymethylphenyl)-6-bromophthalimide | HCID 68491204 | 64% |
| 生成物 | 3-Amino-4,6-di(4-hydroxymethylphenyl)phthalimide | HCID 68492902 | 29% |
反応手順
In a similar manner to Step 2 of Example 2, 3-amino-4-iodo-6-bromophthalimide (100 mg, 0.273 mmol) was dissolved in THF (7 mL), and the solution was treated with 4-hydroxymethylphenylboronic acid (83 mg, 0.55 mmol), tetrakis(triphenylphosphine)palladium (25 mg, 0.022 mmol) and copper(I)thiophene-2-carboxylate (104 mg, 0.546 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 3-amino-4-(hydroxymethylphenyl)-6-bromophthalimide (61 mg, yield 64%) and 3-amino-4,6-di(4-hydroxymethylphenyl)phthalimide (29 mg, yield 29%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745641B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-72bdee8320374be6a672ca3798ce76e8 |
| 出典メモ | uspto-grants-2010_06 |