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Sodium Carbonate → HCID 22319570, Verbindung

HRID 497711
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 497711
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Na+].[Na+].Br[C:19]1[CH:27]=[C:26]2[C:22]([C:23]([NH:36][C:37](=[O:41])[CH2:38][CH2:39][CH3:40])=[N:24][N:25]2[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])=[CH:21][CH:20]=1>O1CCOCC1.C(OCC)(=O)C.O.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:1]([C:3]1[CH:8]=[CH:7][C:6]([C:19]2[CH:27]=[C:26]3[C:22]([C:23]([NH:36][C:37](=[O:41])[CH2:38][CH2:39][CH3:40])=[N:24][N:25]3[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:33])[CH3:34])=[CH:21][CH:20]=2)=[CH:5][CH:4]=1)#[N:2]
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Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 22319559N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

Produkt 1

HCID 22319570HCID 22319570, VerbindungAusbeute 189,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

853 mg of 4-cyanophenylboronic acid, 15 cm3 of water, 1.0 g of sodium carbonate and 314 mg of tetrakis(triphenylphosphine)palladium are added to 500 mg of N-[6-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, prepared as described in Example 51, in 100 cm3 of dioxane. The reaction medium is then refluxed for 4 hours and diluted with 70 cm3 of ethyl acetate and 75 cm3 of water. The organic phase is separated out after settling of the phases has taken place and washed with 50 cm3 of distilled water and then with 2×50 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 45° C.). The residue obtained, 2.0 g, is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 4 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); 1.0 g of N-[6-(4-cyanophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide is obtained in the form of a yellow solid melting at 136° C.

Aufarbeitung

  1. customprepared
  2. temperatureThe reaction medium is then refluxed for 4 hours
  3. customThe organic phase is separated out
  4. washwashed with 50 cm3 of distilled water
  5. customThe organic phase is separated out
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  9. customThe residue obtained
  10. custom2.0 g, is purified by chromatography under an argon pressure of 50 kPa
  11. washon a column of silica gel (particle size 40-60 μm; diameter 4 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  12. additionThe fractions containing the expected product
  13. customevaporated under reduced pressure (2 kPa; 50° C.)

Quellen und Nachweise

ORD-Eintrag
ord-976fb5c7f4eb40648655eafc9d83b823
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06949579B2

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