Triethylamine → 7-[1-(Tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21191

Reaktionsgleichung

Reaktionsgleichung von HRID 21191
IC1C=CC(C)=C2C=1C(=O)NC2.NC1C=CC=C2C=1C(=O)NC2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.C[C:54]1[CH:62]=[CH:61][C:60]([C:63]2[N:64]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[C:65]3[C:70]([CH:71]=2)=[CH:69][C:68]([CH2:72][N:73]2[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]2)=[CH:67][CH:66]=3)=[C:59]2[C:55]=1[CH2:56][NH:57][C:58]2=[O:86]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:82]([O:81][C:79]([N:64]1[C:65]2[C:70](=[CH:69][C:68]([CH2:72][N:73]3[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78]3)=[CH:67][CH:66]=2)[CH:71]=[C:63]1[C:60]1[CH:61]=[CH:62][CH:54]=[C:55]2[C:59]=1[C:58](=[O:86])[NH:57][CH2:56]2)=[O:80])([CH3:85])([CH3:83])[CH3:84]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 162289237-Amino-2,3-dihydro-1H-isoindol-1-oneHCID 684890034-Methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneHCID 684890937-Iodo-4-methylisoindolinone

Produkt 1

HCID 684908137-[1-(Tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 1, a mixture of 7-iodo-4-methylisoindolinone and 7-iodoisoindolinone (10/1, 40.5 mg, 0.149 mmol) was dissolved in acetonitrile (3.24 mL), and the solution was treated with Compound BD (107 mg, 0.298 mmol), palladium acetate (2.7 mg, 0.012 mmol), tri(o-tolyl)phosphine (7.3 mg, 0.024 mmol) and triethylamine (0.208 mL, 1.49 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1) to obtain a mixture of 4-methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone and 7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (38.2 mg, ratio 92.9/7.1, yield 56%). 4-methyl-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=12/1)
  2. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-fd568bdb36544647841062cdafaa8ae0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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