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HCID 67960127, Verbindung → HCID 67959731, Verbindung

HRID 1529367
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1529367
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=[C:7]2I)(=[O:3])[NH2:2].C([Sn](CCCC)(CCCC)[C:26]1[N:31]=[C:30]([N:32]2[CH2:37][CH2:36][CH:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:34][CH2:33]2)[CH:29]=[N:28][CH:27]=1)CCC>CN(C=O)C.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:41]([O:40][C:39]([NH:38][CH:35]1[CH2:36][CH2:37][N:32]([C:30]2[N:31]=[C:26]([C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([C:1](=[O:3])[NH2:2])[CH:5]=4)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=3)[CH:27]=[N:28][CH:29]=2)[CH2:33][CH2:34]1)=[O:45])([CH3:44])([CH3:42])[CH3:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 67960127HCID 67960127, VerbindungHCID 86709776HCID 86709776, Verbindung

Produkt 1

HCID 67959731HCID 67959731, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of tert-butyl 5-carbamoyl-3-iodo-1H-indole-1-carboxylate (460 mg, 1.42 mmol) and tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-4-ylcarbamate (1d) (807 mg, 1.42 mmol) in DMF (4.6 mL) was purged with argon gas for 5 min, added Cut (405 mg, 2.13 mmol), palladium tetrakis (170 mg, 0.14 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, which was purified by column chromatography to obtain the title compound as a brown solid (200 mg, 31%). MS (ESI, pos. ion) m/z: 537.0 (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, which
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ec8ec0b3b65a4e5fa39b544a08893d22
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090593B2

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