反応式
Br[C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[I-:22].[K+].[Cl-].[NH4+]>CN(C)P(=O)(N(C)C)N(C)C>[I:22][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 160 °C
実験手順
A mixture of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (530 mg, 1.50 mmol), potassium iodide (4.98 g, 30 mmol) and cuprous iodide (2.0 g, 10.5 mmol) in hexamethylphosphoric triamide (5 mL) was heated at 160° C. for 6.5 h and poured into 1N aqueous ammonium chloride (200 mL). The mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL). The extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL), dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 0.7 to 1% acetic acid/ethyl acetate to give 465 mg of the title compound (78%): mp 241°~243° C.; 1H NMR (270 MHz, DMSO-d6) δ12.01 (bs, 1H), 7.33 (s, 1H), 7.31 (s, 1H), 5.03~5.14 (m, 1H), 3.62 (s, 3H), 2.93 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.78 (dm, 1H, J=17.1 Hz), 2.54~2.69 (m, 2H), 2.09 (dm, 1H, J=13.5 Hz), 1.79~1.96 (m, 1H).
後処理
- extractionThe mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL)
- washThe extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography with 0.7 to 1% acetic acid/ethyl acetate
出典と根拠
- ORDレコード
- ord-c0190e97826d4368a378ca9e65e3bdc0
- 出典データセット
- uspto-grants-1997_04
- 特許番号
- US05616586
関連ノート
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