Sodium Carbonate → HCID 59970488, Verbindung

HRID 380023

Reaktionsgleichung

Reaktionsgleichung von HRID 380023
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)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>[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH2:33])=[O:32])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 16074N-(4-Bromophenyl)ureaHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Produkt 1

HCID 59970488HCID 59970488, VerbindungAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 4-bromophenylurea (0.16 g), 2M aqueous sodium carbonate (0.25 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in ethanol (3 ml). The reaction mixture was heated at 100° C. for 3 hours. After cooling, the solution was concentrated under reduced pressure. The residue was triturated with acetone and then filtered through silica gel. The filtrate was concentrated under reduced pressure and purified by flash column chromatography eluting with 10% methanol in dichloromethane give the title compound as a solid (0.046 g).

Aufarbeitung

  1. customPrepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe residue was triturated with acetone
  5. filtrationfiltered through silica gel
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by flash column chromatography
  8. washeluting with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cd53f23750b7440aae6352185cf0202b
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300352B1

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