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Piperidine → HCID 44539730, Verbindung

HRID 1616034
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1616034
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])=[N:6][CH:7]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CS(C)=O.CO>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:5]4[CH:4]=[CH:3][C:2]([N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:7][N:6]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 44540317HCID 44540317, Verbindung

Produkt 1

HCID 44539730HCID 44539730, VerbindungAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

5-Bromo-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (50 mg, 0.12 mmol) and piperidine (1 ml, 10.1 mmol) were placed in a microwave vial. Pd2dba3 (5 mg, 0.006 mmol), BINAP (7.2 mg, 0.012 mmol) and cesium carbonate (57 mg, 0.17 mmol) were added and the mixture was heated at 150° C. for 75 mins under microwave irradiation. The reaction mixture was concentrated in vacuo to give a crude residue that was suspended in 1:1 DMSO/MeOH (1 ml) and filtered to give an orange solution that was purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with MeOH and the solvent removed under a stream of nitrogen to give the title compound (18 mg) as a yellow gum.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a crude residue that
  3. filtrationfiltered
  4. customto give an orange solution that
  5. customwas purified by Mass Directed Automated Preparative HPLC (Method C)
  6. washeluted with MeOH
  7. customthe solvent removed under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-7d1322573fd546b7a02f9cb439e4feef
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765743B2

Notizen zur Reaktion

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