Allyl chloroformate → carbonic acid allyl ester 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 411775

Reaction equation

[OH:1][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[C:5]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)[C:4]1=[O:32].Cl[C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35].N12CCCC1=NCCC2>C1COCC1.CN(C)C1C=CN=CC=1>[CH3:31][N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:5]2[C:4](=[O:32])[N:3]([CH2:2][O:1][C:34](=[O:35])[O:36][CH2:37][CH:38]=[CH2:39])[C:7](=[O:8])[C:6]=2[C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[CH:23]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 200 mg (0.47 mmole) of 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione, prepared as in the example 1a, was dissolved in 90 ml of THF and treated with 300 mg (2.5 mmol) of 4-dimethylaminopyridine (DMAP). To this solution at 5° C. was added 90 mg (0.75 mmole) of allyl chloroformate. While still cool, 300 mg (2.4 mmol) of 1,5-diazabicyclo(4.3.0)non-5-ene (DBN) (Aldrich) was added dropwise. This was stirred for 14 hours at 20° C. The solvent was evaporated and the mixture was purified by chromatography using silica gel and eluting with a mixture of EtOAc/Hexane to afford carbonic acid allyl ester 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 as a red solid (m.p. 191-194° C.).

Workup

temperatureWhile still cool
customThe solvent was evaporated
customthe mixture was purified by chromatography
washeluting with a mixture of EtOAc/Hexane

Sources & evidence

ORD record: ord-d1c3c1a6b7464bf3bd30b0ed91da6c77
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559164B1

Linked notes

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