Triethylamine → HCID 68492358, compound

HRID 21120Notes

Reaction equation

HRID 21120 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].[C:13]([O:17][C:18]([N:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]#[N:30])=[CH:26][CH:27]=2)[CH:22]=[C:21]1B(O)O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(#N)C.CCCCCC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:21]2[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[C:28]3[C:23]([CH:22]=2)=[CH:24][C:25]([C:29]#[N:30])=[CH:26][CH:27]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 42364971-Boc-5-cyano-1H-indole-2-boronic acidHCID 684927354-Chloro-7-iodoisoindolinone

Product 1

HCID 68492358HCID 68492358, compoundYield 42.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a similar manner to Step 2 of Example 1, 4-chloro-7-iodoisoindolinone (68.4 mg, 0.230 mmol) was dissolved in acetonitrile (1.4 mL), and the solution was treated with 1-(tert-butoxycarbonyl)-5-cyanoindole-2-boronic acid (100 mg, 0.350 mmol) synthesized in a similar manner to the method described in Journal of Organic Chemistry, 2002, vol. 67, p. 7551, palladium acetate (4.1 mg, 0.018 mmol) and triethylamine (0.321 mL, 2.30 mmol), followed by purification by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-cyanoindol-2-yl]isoindolinone (40.2 mg).

Workup

  1. customsynthesized in a similar manner to the method

Sources & evidence

ORD record
ord-44c73f9243594799bab685f213e741bb
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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