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Potassium Carbonate → HCID 86700867, Verbindung

HRID 881760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 881760
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][CH:11]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:37]1[CH2:42][CH2:41][C:40]([C:48]([O:50][CH2:51][CH3:52])=[O:49])([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:39][CH:38]=1)(=O)=O>O1CCOCC1.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>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:37]3[CH2:42][CH2:41][C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:39][CH:38]=3)=[CH:14][CH:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 86692328HCID 86692328, VerbindungHCID 86700866HCID 86700866, Verbindung

Produkt 1

HCID 86700867HCID 86700867, VerbindungAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A flask was charged with 5-nitro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.9 g, 10.73 mmol) and potassium carbonate (6.77 g, 48.3 mmol) in dioxane (60 ml) and Water (25 ml), and stirred at room temperature for 10 minutes under nitrogen. Then Pd(PPh3)4 (1.240 g, 1.073 mmol) and diethyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-ene-1,1-dicarboxylate (4.22 g, 11.27 mmol) were added to the reaction mixture. The flask was sealed, flushed with nitrogen for three times and heated at 100° C. for 1 hour. The organic solvent was evaporated under vacuum and EtOAc (3×100 ml) was used to extract and the combined organic solvent was washed by saturated aqueous sodium bicarbonate solution, brine, and dried over Na2SO4, then concentrated. The residue was purified by flash chromatography (heptanes/acetone 1/2) to afford diethyl 4′-(5-nitropyridin-2-yl)-5,6-dihydro-[1,1′-biphenyl]-4,4(3H)-dicarboxylate (2.8 g, 61%) as yellow solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.25 (t, J=7.20 Hz, 6H) 2.30 (dt, J=6.28, 3.24 Hz, 2H) 2.53 (dd, J=4.67, 1.77 Hz, 2H) 2.76 (dd, J=3.98, 2.08 Hz, 2H) 4.20 (q, J=7.20 Hz, 4H) 6.19 (s, 1H) 7.06-8.88 (m, 7H).

Aufarbeitung

  1. customThe flask was sealed
  2. customflushed with nitrogen for three times
  3. temperatureheated at 100° C. for 1 hour
  4. customThe organic solvent was evaporated under vacuum and EtOAc (3×100 ml)
  5. extractionto extract
  6. washthe combined organic solvent was washed by saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (heptanes/acetone 1/2)

Quellen und Nachweise

ORD-Eintrag
ord-8095dd3c7880400695bf5dbd7180b5d5
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993619B2

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