Sodium Carbonate → Ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

HRID 749145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749145
FC(F)(F)S(O[C:7]1[CH2:14][CH:13]2[CH2:15][CH:9]([CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]2)[CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].[O:31]([C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[N:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>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>[O:31]([C:38]1[CH:39]=[C:40]([C:7]2[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]3)[CH:8]=2)[CH:41]=[N:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 53401497(5-Phenoxypyridin-3-yl)boronic acidHCID 57486348Ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

Produkt 1

HCID 57486354Ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1] non-6-ene-3-carboxylate (0.13 g, 0.38 mmol) in dimethoxyethane (3 mL) was added saturated sodium carbonate solution (1 mL), lithium chloride (0.04 g, 0.9 mmol) and 5-phenoxy-3-pyridinylboronic acid (0.17 g, 0.79 mmol). The flask was alternately evacuated and filled with argon three times. Then, tetrakis(triphenylphosphine)palladium(0) (0.01 g, 0.01 mmol) was added, and the evacuation and argon fill was performed once again. The flask was sealed under argon, and the stirred reaction mixture was heated at 95(C for 2 h. The mixture was cooled to ambient temperature, diluted with water (10 mL), extracted with chloroform (3×5 mL). The extracts were dried over sodium sulfate and filtered. Concentration of the filtrate by rotary evaporation, followed by purification of the residue by silica gel column chromatography, using a gradient of 0-2% methanol in chloroform/as eluent, gave ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate as a light yellow oil (0.12 g, 87%).

Aufarbeitung

  1. customThe flask was alternately evacuated
  2. additionfilled with argon three times
  3. customThe flask was sealed under argon
  4. customthe stirred reaction mixture
  5. temperaturewas heated at 95(C for 2 h
  6. extractionextracted with chloroform (3×5 mL)
  7. dry with materialThe extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customConcentration of the filtrate by rotary evaporation
  10. customfollowed by purification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-784cac9988bd424db9e9fab4d4ca484d
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402592B2

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