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HCID 67959759, Verbindung → HCID 67959959, Verbindung

HRID 1529363
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1529363
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:27]1[N:32]=[C:31]([N:33]2[CH2:38][CH2:37][CH:36]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:35][CH2:34]2)[CH:30]=[N:29][CH:28]=1)CCC>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:42]([O:41][C:40]([NH:39][CH:36]1[CH2:37][CH2:38][N:33]([C:31]2[N:32]=[C:27]([C:2]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=4)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=3)[CH:28]=[N:29][CH:30]=2)[CH2:34][CH2:35]1)=[O:46])([CH3:45])([CH3:43])[CH3:44]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 67959759HCID 67959759, VerbindungHCID 86709776HCID 86709776, Verbindung

Produkt 1

HCID 67959959HCID 67959959, VerbindungAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-tert-butyl 5-methyl 3-iodo-1H-indole-1,5-dicarboxylate (6 g, 14.96 mmol) and tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-4-ylcarbamate (1d) (10.2 g, 17.95 mmol) in DMF (60 mL) was purged with argon gas for 5 min, added CuI (4.27 g, 22.44 mmol), palladium tetrakis (1.7 g, 1.5 mmol) and again purged with argon gas for 5 min. The reaction mixture was stirred at 90° C. under nitrogen atmosphere for 1 h. The reaction mixture was then poured into water. The resulting precipitate was collected by filtration. The filtrate was extracted with diethyl ether. The organic layer was concentrated and combined with the above precipitate to give the crude product. Purification was carried out by column chromatography to obtain the title compound as a brown solid (2.5 g, 30%). MS (ESI, pos. ion) m/z: 552.2 (M+1).

Aufarbeitung

  1. customwas purged with argon gas for 5 min
  2. customagain purged with argon gas for 5 min
  3. additionThe reaction mixture was then poured into water
  4. filtrationThe resulting precipitate was collected by filtration
  5. extractionThe filtrate was extracted with diethyl ether
  6. concentrationThe organic layer was concentrated
  7. customto give the crude product
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-2ca011affbb4469c8c25b8ac75d89e83
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090593B2

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