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Ethyl Acetate → 4-{4-[6,7-Bis(methyloxy)quinolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-2-nitroaniline
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 2-Nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 16217914 | — |
| 反応物 | 4-[6,7-Bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine | HCID 66819980 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 生成物 | 4-{4-[6,7-Bis(methyloxy)quinolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-2-nitroaniline | HCID 66820277 | 63% |
反応手順
A mixture 4-[6,7-bis(methyloxy)quinolin-4-yl]-7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine (78 mg, 0.19 mmol), 4-amino-3-nitrophenylboronic acid pinacol ester (59 mg, 0.23 mmol), potassium carbonate (105 mg, 0.76 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (20 mg, 0.02 mmol) in dimethoxyethane (3 mL) was stirred at 80° C. for 3 h. Ethyl acetate (50 mL) was added and the mixture was washed with water (20 mL), and brine (20 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (dichloromethane:methanol 95:5) gave 4-{4-[6,7-bis(methyloxy)quinolin-4-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl}-2-nitroaniline (56 mg, 63% yield). MS (EI) for C26H24N4O5: 473 (MH+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08648066B2 |
| 出典データセット | uspto-grants-2014_02 |
| ORD ID | ord-2878c72d97e0445896b4cf842ea621cf |
| 出典メモ | uspto-grants-2014_02 |