Dimethylformamide → decanoic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

HRID 411772

反応式

HRID 411772 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:30])[NH:13][C:14](=[O:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[CH:3]1.[C:31]([O-:34])([O-])=O.[Cs+].[Cs+].CN([CH:40]=[O:41])C>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:30])[N:13]([CH2:31][O:34][C:40](=[O:41])[CH2:15][CH2:11][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:14](=[O:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[CH:3]1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 53276861H-pyrrole-2,5-dione, 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-

生成物 1

HCID 9851329decanoic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester収率 58%

実験手順

3-(1-Methyl-3-indolyl)-4-(1-methyl-6-nitro-3-indolyl)-1H-pyrrole-2,5-dione (20 mg 0.05 mmol) (See Davis U.S. Pat. No. 5,057,614) was dissolved in DMF and treated with Cs2CO3 (49 mg, 0.15 mmol) for a few minutes, the chloromethyl ester (33 mg, 0.15 mmol) prepared in step a) above was added and the reaction was stirred at room temperature for 30 minutes. Aqueous workup, followed by purification by flash chromatography yielded decanoic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (yield—58%).

後処理

  1. customAqueous workup, followed by purification by flash chromatography

出典と根拠

ORDレコード
ord-03c6aa2ad9ce48129335bdd5a99be1db
出典データセット
uspto-grants-2003_05
特許番号
US06559164B1

関連ノート

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