2-Bromo-5-(1,3-oxazol-2-yl)benzaldehyde → HCID 15895425, Verbindung

HRID 1637707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637707
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[C:24]([CH3:25])=[C:23]([CH3:26])[O:22][N:21]=1)[CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])(=[O:12])=[O:11])(O)O.Br[C:28]1[CH:35]=[CH:34][C:33]([C:36]2[O:37][CH:38]=[CH:39][N:40]=2)=[CH:32][C:29]=1[CH:30]=[O:31]>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O.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>[CH3:25][C:24]1[C:20]([N:13]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[S:10]([C:5]2[C:4]([C:28]3[CH:35]=[CH:34][C:33]([C:36]4[O:37][CH:38]=[CH:39][N:40]=4)=[CH:32][C:29]=3[CH:30]=[O:31])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:12])=[O:11])=[N:21][O:22][C:23]=1[CH3:26]

Komponenten

8

Edukt 2

HCID 107059332-Bromo-5-(1,3-oxazol-2-yl)benzaldehydeHCID 11728709B-[2-[[(4,5-dimethyl-3-isoxazolyl)[(2-methoxyethoxy)methyl]amino]sulfonyl]phenyl]Boronic acid

Produkt 1

HCID 15895425HCID 15895425, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To the 2-borono-N-(4,5-dimethyl-3-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide and 2-bromo-5-(2-oxazolyl)benzaldehyde (13.32 g, 58.14 mmol, prepared as described in Example 21 of European Patent Application No. 702,012) in 264 ml of toluene and 132 ml of 95% ethanol ("EtOH"), 106 ml 2M aqueous sodium carbonate and tetrakis(triphenylphosphine)palladium(0) (6.11 g, 5.29 mmol) were added and the reaction mixture heated under argon at 85° C. for 4 hrs, cooled and diluted with 250 ml of EtOAc. The organic layer was separated and washed with 100 ml H2O and 50 ml brine, dried and concentrated. The residue was chromatographed on silica gel using 1:1 hexane/EtOAc to afford the title product of this step (16.95 g, 62.7% for two steps) as a colorless gum.

Aufarbeitung

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with 100 ml H2O and 50 ml brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 1:1 hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-4667c5e162a44d8eaa4b3b625088fc19
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043265

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