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tert-Butyl 3-iodo-5-nitro-1H-indole-1-carboxylate → HCID 67959775, Verbindung

HRID 1529355
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1529355
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](I)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].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:10]3[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=4)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=3)[CH:27]=[N:28][CH:29]=2)[CH2:33][CH2:34]1)=[O:45])([CH3:44])([CH3:42])[CH3:43]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 40428559tert-Butyl 3-iodo-5-nitro-1H-indole-1-carboxylateHCID 86709776HCID 86709776, Verbindung

Produkt 1

HCID 67959775HCID 67959775, VerbindungAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a mixture of 3-Iodo-5-nitro-indole-1-carboxylic acid tert-butyl ester (480 mg, 1.23 mmol) and tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-4-ylcarbamate 1d (700 mg, 1.23 mmol) in DMF (4.8 mL) was purged with argon gas for 5 min and added Cut (352 mg, 1.84 mmol) and palladium tetrakis (171 mg, 0.15 mmol). The resulting mixture was purged with argon gas for 5 min and stiffed under nitrogen atmosphere at 90° C. 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 white solid (200 mg, 30%). MS (ESI, pos. ion) m/z: 539.3 (M+1).

Aufarbeitung

  1. customwas purged with argon gas for 5 min
  2. customThe resulting mixture was 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-f556da950a244f36a015c6e3baa701cb
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090593B2

Notizen zur Reaktion

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