Water → HCID 178517259, compound

HRID 1637962Notes

Reaction equation

HRID 1637962 reaction equation
Cl[C:2](=[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=2)[NH:12][C:11]1=[O:22])[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.[N:23]1([CH2:28][C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.O>CN(C=O)C.C(Cl)Cl.CO>[N:23]1([CH2:28][C:29]2[CH:35]=[CH:34][C:32]([NH:33]/[C:2](=[C:10]3\[C:11](=[O:22])[NH:12][C:13]4[C:18]\3=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=4)/[C:3]3[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=3)=[CH:31][CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7768524-(Pyrrolidin-1-ylmethyl)anilineHCID 54283663HCID 54283663, compound

Product 1

HCID 178517259HCID 178517259, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared by reacting 3-[1-chloro-1-(4-bromo-phenyl)methylidene]-5-nitro-2-indolinone with 1 equivalent of 4-(pyrrolidin-1-yl-methyl)aniline and 2 equivalents of Hunig's base in DMF (1 hours, 120° C.), pouring into water, extraction with EtOac, separation of the organic phase and purification thereof by column chromatography on SiO2 with CH2Cl2 /MeOH (15:1) as eluant.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-29c4d9ad0ee44b2ca56c15fa6e762f89
Source dataset
uspto-grants-2000_03
Patent number
US06043254

Reaction notes

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