Sodium Carbonate → N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

HRID 1988926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988926
[CH:1]1([CH2:4][NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:8]=2)[CH2:3]C1.Br[C:24]1[CH:39]=[CH:38][C:27]2[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=2[CH:25]=1.[C:40](=O)([O-])[O-].[Na+].[Na+]>C(O)(C)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>[CH:4]1([NH:5][C:6](=[O:22])[C:7]2[CH:12]=[CH:11][C:10]([CH3:40])=[C:9]([C:24]3[CH:39]=[CH:38][C:27]4[C:28]([CH2:31][C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[N:29][O:30][C:26]=4[CH:25]=3)[CH:8]=2)[CH2:1][CH2:3]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 586564962-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide2×HCID 68676775HCID 68676775, Verbindung2×

Produkt 1

HCID 10453183N-Cyclopropyl-3-(3-{2-[(2-hydroxyethyl)amino]-2-oxoethyl}-1,2-benzisoxazol-6-yl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 5) (0.04 g) 2-(6-bromo-1,2-benzisoxazol-3-yl)-N-(2-hydroxyethyl)acetamide (Intermediate 35) (0.04 g) 2M aqueous sodium carbonate (1.5 ml) and tetrakis(triphenylphosphine)palladium(0) (1 mg) in isopropanol (3 ml) was stirred at reflux under nitrogen for 18 h. The mixture was absorbed onto silica (Merck 7734) and applied to a Varian Bond-Elut SPE cartridge (silica, 5 g) and eluted with a toluene:ethanol gradient (100:0 to 0:100) to give the title compound as a white solid (0.03 g).

Aufarbeitung

  1. temperatureat reflux under nitrogen for 18 h
  2. customThe mixture was absorbed onto silica (Merck 7734)
  3. washeluted with a toluene

Quellen und Nachweise

ORD-Eintrag
ord-f8dd1ace81eb419484916977c6880292
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642276B2

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