Sodium Carbonate → N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

HRID 1988923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988923
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[CH:5]2.[CH:18]1([CH2:21][NH:22][C:23](=[O:39])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:20]C1.[C:40](=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]1([NH:22][C:23](=[O:39])[C:24]2[CH:25]=[CH:26][C:27]([CH3:40])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[NH:7][N:6]=[CH:5]4)[CH:29]=2)[CH2:18][CH2:20]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 228320255-Bromo-1H-indazole, N1-BOC protected2×HCID 68676775HCID 68676775, Verbindung2×

Produkt 1

HCID 10469531N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 3, 2.0 g) and N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 5, 2.04 g) in DME (125 ml) was added tetrakis (triphenylphosphine) palladium (0.78 g) and aqueous sodium carbonate (1M, 80 ml). The mixture was heated at reflux under nitrogen for 16 h. The solvent was evaporated and the residue was purified by column chromatography on silica, eluting with cyclohexane:ethyl acetate (2:1 to 1:1) to give the title compound (1.38 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 16 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica
  5. washeluting with cyclohexane:ethyl acetate (2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d95121f2ee3e412993db9d86bac97647
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642276B2

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