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

Reaction equation

HRID 411772 reaction equation
[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

Participants

4

Reactant 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)-

Product 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 esterYield 58%

Procedure

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%).

Workup

  1. customAqueous workup, followed by purification by flash chromatography

Sources & evidence

ORD record
ord-03c6aa2ad9ce48129335bdd5a99be1db
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Linked notes

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