Triethylamine → 4-Chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone

HRID 21009

Reaktionsgleichung

Reaktionsgleichung von HRID 21009
[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][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1B(O)O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)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: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][CH:25]=[CH:26][CH:27]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 684927354-Chloro-7-iodoisoindolinone

Produkt 1

HCID 684875944-Chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinoneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 1, 4-chloro-7-iodoisoindolinone (100 mg, 0.341 mmol) was dissolved in acetonitrile (7 mL), and the solution was treated with 1-(tert-butoxycarbonyl)indol-2-boronic acid (178 mg, 0.682 mmol), palladium acetate (6.1 mg, 0.027 mmol), tri(o-tolyl)phosphine (17 mg, 0.055 mmol) and triethylamine (0.475-mL, 3.41 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=30/1) to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone (57 mg, yield 44%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=30/1)

Quellen und Nachweise

ORD-Eintrag
ord-5119cba16e984a6aab5c271874fb30e8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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