Sodium Carbonate → tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

HRID 598887

Reaktionsgleichung

Reaktionsgleichung von HRID 598887
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:6]=1.CC1(C)C(C)(C)OB([C:34]2[CH:43]=[CH:42][C:37]3[NH:38][C:39](=[O:41])[O:40][C:36]=3[CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1>COCCOC.CCO.O.C([O-])(O)=O.[Na+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([C:34]3[CH:43]=[CH:42][C:37]4[NH:38][C:39](=[O:41])[O:40][C:36]=4[CH:35]=3)[CH:3]=[N:4]2)=[CH:12][CH:13]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 579506376-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-oneHCID 57950651HCID 57950651, Verbindung

Produkt 1

HCID 68373025tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 516892Sodium BicarbonateLösungsmittelHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of (S)-tert-butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamate (200 mg, 0.47 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (183 mg, 0.70 mmol), sodium carbonate (148 mg, 1.40 mmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (34.0 mg, 0.09 mmol), and bis(dibenzylideneacetone)palladium(0) (42.7 mg, 0.05 mmol) in DME:EtOH:H2O (7:2:3, 4 mL) was heated at 130° C. for 15 minutes in a Biotage Initiators microwave. After cooling to room temperature, the mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The material thus obtained was used without further purification.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material thus obtained
  7. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-0c5b5cb5643b453bacc6f0195b49577b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897619B2

Verknüpfte Notizen

Wird geladen…