Sodium Carbonate → HCID 59127378, Verbindung

HRID 1988930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988930
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]2.[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28](B(O)O)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]4)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 21914527(5-(Cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)boronic acid2×HCID 228320255-Bromo-1H-indazole, N1-BOC protected2×

Produkt 1

HCID 59127378HCID 59127378, VerbindungAusbeute 211,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 3) (1.07 g) {5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (Intermediate 64) (0.85 g) sodium carbonate (1.9 g) and tetrakis(triphenylphosphine)palladium(0) (0.42 g) in 1,2-dimethoxyethane (70 ml) was stirred at reflux under nitrogen for 20 h. the solvent was removed and the residue was partitioned between water (50 ml) and ethyl acetate (50 ml). The aqueous layer was re-extracted with ethyl acetate (3×30 ml) and the combined organic extracts were dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40) to give the title compound (3.1 g).

Aufarbeitung

  1. temperatureat reflux under nitrogen for 20 h. the solvent
  2. customwas removed
  3. customthe residue was partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (3×30 ml)
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-619e0ebd5a0a4a9584822b60f52bd3a9
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642276B2

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