Triethylamine → Phthalimide

HRID 21004

Reaktionsgleichung

Reaktionsgleichung von HRID 21004
N[C:2]1[C:12](/C=C/C(OC)=O)=[CH:11][C:10](Br)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:8]1(=[O:9])[NH:7][C:5](=[O:6])[C:4]2=[CH:10][CH:11]=[CH:12][CH:2]=[C:3]12

Komponenten

6

Edukt 2

HCID 8471TriethylamineHCID 68491786(E)-3-amino-4-(2-methoxycarbonylvinyl)-6-bromophthalimide

Produkt 1

HCID 6809PhthalimideAusbeute 225,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 1, (E)-3-amino-4-(2-methoxycarbonylvinyl)-6-bromophthalimide (100 mg, 0.308 mmol) was dissolved in acetonitrile (7 mL), and the solution was treated with Compound BB (292 mg, 0.616 mmol), palladium acetate (5.5 mg, 0.025 mmol), tri(o-tolyl)phosphine (15 mg, 0.049 mmol) and triethylamine (0.429 mL, 3.08 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=6/1) to obtain (E)-3-amino-4-(2-methoxycarbonylvinyl)-6-(tert-butoxycarbonyl)-5-[4-(tert-butoxycarbonyl)piperazin-1-ylcarbonyl]indol-2-yl)phthalimide (102 mg, yield 49%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=6/1)

Quellen und Nachweise

ORD-Eintrag
ord-bacf4084fd1e45ed9900c8c00955c92f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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