Sodium Carbonate → HCID 69357909, Verbindung

HRID 1272127

Reaktionsgleichung

Reaktionsgleichung von HRID 1272127
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH3:22])=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[Na+].[Na+].CB1OB(C)OB(C)O1.[OH-].[Na+]>C(COC)OC.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>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH3:22])=[C:14]([CH3:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 574072TrimethylboroxineHCID 69357585(4R,9aR)-7-Bromo-4,6-dimethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 69357909HCID 69357909, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.30 g (0.78 mmol) (4R,9aR)-7-bromo-4,6-dimethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (example 6, intermediate) in 15 mL dimethoxyethane was added 9 mg tetrakis(triphenylphosphine)palladium. After 20 min. 0.25 g (2.35 mmol) sodium carbonate in 8 mL water and 132 μl (0.94 mmol) trimethylboroxine were added and the reaction was stirred at 100° C. for 3 h. The reaction was cooled to room temperature then poured into 1M aqueous sodium hydroxide solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel with ethyl acetate:n-hexane (1:2) as eluant to give the product as a light yellow oil (66.0%).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel with ethyl acetate:n-hexane (1:2) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-a3d843c290264c8b80d9c6c2fa7ecab9
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208494B2

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