Hydrochloric Acid → HCID 59340101, Verbindung

HRID 905905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905905
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:22])=[C:7]([C:14]([NH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:15])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][CH:3]=1.[CH3:23][C:24]1[C:28](B(O)O)=[C:27]([CH3:32])[O:26][N:25]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>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.C(Cl)(Cl)Cl.CN(C=O)C>[CH3:23][C:24]1[C:28]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([OH:22])=[C:7]([C:14]([NH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:15])[C:8](=[O:13])[N:9]3[CH3:12])=[CH:4][CH:3]=2)=[C:27]([CH3:32])[O:26][N:25]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 54681697Methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

Produkt 1

HCID 59340101HCID 59340101, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (400 mg, 1084 μmol), 3,5-dimethylisoxazol-4-ylboronic acid (305 mg, 2167 μmol) and Pd(PPh3)4 (125 mg, 108 μmol) in 8 ml 1,2-dimethoxyethane (or DMF) and 1.6 ml 2M aqueous Na2CO3 was heated to 75° C. and stirred for 12 hours. The mixture was cooled to 24° C., treated with 1M aqueous HCl and CHCl3, after which solids precipitated. The organic layer was separated and the solids were collected by filtration, and washed with MeOH.

Aufarbeitung

  1. temperatureThe mixture was cooled to 24° C.
  2. customafter which solids precipitated
  3. customThe organic layer was separated
  4. filtrationthe solids were collected by filtration
  5. washwashed with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-82a42480bc95417499d5f1cc4bfcd055
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012968B2

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