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Potassium Carbonate → HCID 67201862, Verbindung

HRID 1888531
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1888531
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C12BC(CCC1)CCC2.[C:24]1([S:30]([N:33]2[C:37]3[CH:38]=[N:39][C:40]([C:43]#[N:44])=[C:41](Br)[C:36]=3[C:35]3[CH:45]=[CH:46][CH:47]=[N:48][C:34]2=3)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C.ClCCl.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:41]2[C:36]3[C:35]4[CH:45]=[CH:46][CH:47]=[N:48][C:34]=4[N:33]([S:30]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)(=[O:32])=[O:31])[C:37]=3[CH:38]=[N:39][C:40]=2[C:43]#[N:44])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 27568081-Boc-4-MethylenepiperidineHCID 58266792HCID 58266792, Verbindung

Produkt 1

HCID 67201862HCID 67201862, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178477754
HCID 178477754, Verbindung
Katalysator
HCID 962WaterLösungsmittel2×
HCID 6228DimethylformamideLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4-methylene-piperidine-1-carboxylic acid tert-butyl ester (0.70 g, 3.55 mmol) and 9-borabicyclo[3,3,1]nonane (0.5M solution in THF, 7 mL, 3.5 mmol) were heated at reflux for 1.5 h. The reaction mixture was cooled and added to a degassed mixture of 9-benzenesulfonyl-5-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (0.41 g, 1.0 mmol), [1,1-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (0.090 g, 0.11 mmol) and potassium carbonate (0.18 g, 1.3 mmol) in water (1 mL) and DMF (10 mL) and the reaction mixture was then heated at 65° C. for 1.25 h. After cooling to ambient temperature the reaction mixture was then diluted with water (5 mL) and dichloromethane (10 mL). The aqueous phase was extracted with dichloromethane (2×15 mL) and the combined organic phase was washed with brine (15 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with pentane (10 mL) and the resultant material was purified by flash chromatography (silica, 5 g column, SPE-Si II, 0-2% methanol in DCM) to afford title compound as a yellow solid (202 mg, 38%). 1H NMR (CDCl3, 400 MHz): 9.81 (s, 1H), 8.79 (dd, J=4.8, 1.6 Hz, 1H), 8.33-8.27 (m, 3H), 7.66-7.60 (m, 1H), 7.55-7.46 (m, 3H), 4.22-4.01 (m, 2H), 3.34-3.27 (m, 2H), 2.62-2.50 (m, 2H), 1.97-1.76 (m, 2H), 1.72-1.46 (m, 3H), 1.45 (s, 9H).

Aufarbeitung

  1. temperaturewere heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. temperatureAfter cooling to ambient temperature the reaction mixture
  5. extractionThe aqueous phase was extracted with dichloromethane (2×15 mL)
  6. washthe combined organic phase was washed with brine (15 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with pentane (10 mL)
  11. customthe resultant material was purified by flash chromatography (silica, 5 g column, SPE-Si II, 0-2% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-80509290003d407cb9728c709aef8aa6
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501765B2

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