Triethylamine → 4-Chloro-7-(1-methylindol-2-yl)isoindolinone

HRID 21103Notes

Reaction equation

HRID 21103 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](I)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:16]2[N:15]([CH3:13])[C:18]3[C:19]([CH:17]=2)=[CH:4][CH:3]=[CH:2][CH:10]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 684927354-Chloro-7-iodoisoindolinone

Product 1

HCID 684922684-Chloro-7-(1-methylindol-2-yl)isoindolinoneYield 164.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 2 of Example 1, 4-chloro-7-iodoisoindolinone (84.0 mg, 0.286 mmol) was dissolved in acetonitrile (3 mL), and the solution was treated with Compound BK (100 mg, 0.571 mmol), palladium acetate (5.2 mg, 0.023 mmol) and triethylamine (0.400 mL, 2.87 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=7/3, 3/2, 1/1) to obtain Compound 156 (69.7 mg, yield 82%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=7/3, 3/2, 1/1)

Sources & evidence

ORD record
ord-62ee8151a279485585f17aa92ecaaf07
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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