関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 4-Bromo-2-methylisoquinolin-1(2H)-one | HCID 311858 | — |
| 反応物 | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 4-(3-Methoxyphenyl)-2-methylisoquinolin-1-one | HCID 118021804 | 17% |
反応手順
A mixture of 4-bromo-2-methylisoquinolin-1(2H)-one (100 mg, 0.42 mmol), and (3-methoxyphenyl)boronic acid (70 mg, 0.46 mmol), PPh3 (66 mg, 0.25 mmol), Na2CO3 (133 mg, 1.26 mmol), and Pd(dppf)Cl2 (62 mg, 0.084 mmol) in dioxane (2.5 mL) and water (0.5 mL) was heated overnight at 90° C. Extractive work up with ethyl acetate followed by preparative TLC (PE:EA=1:1) gave the title compound (18 mg, 0.07 mmol) as a white solid in 17% yield. 1H NMR (DMSO, 400 MHz): δ 8.30 (d, 1H, J=7.68), 7.68 (t, 1H, J=7.56), 7.50-7.55 (m, 3H), 7.40 (t, 1H, J=7.44), 6.97-7.00 (m, 3H), 3.78 (s, 3H), 3.54 (s, 3H). MS (m/z, relative intensity): 266 (M+, 1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09115114B2 |
|---|
| 出典データセット | uspto-grants-2015_08 |
|---|
| ORD ID | ord-63dd6400b217496985de570a857326c0 |
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| 出典メモ | uspto-grants-2015_08 |
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