Potassium Carbonate → 10-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

HRID 2092705

Reaktionsgleichung

Reaktionsgleichung von HRID 2092705
[O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][NH:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[C:23]1[CH:33]=[CH:32][C:26]2[O:27][C:28]([F:31])([F:30])[O:29][C:25]=2[CH:24]=1>C1(C)C=CC=CC=1>[F:31][C:28]1([F:30])[O:27][C:26]2[CH:32]=[CH:33][C:23]([N:10]3[CH2:11][CH2:12][C:8]4([CH2:14][CH2:15][C:5]5([O:4][CH2:3][CH2:2][O:1]5)[CH2:6][CH2:7]4)[C:9]3=[O:13])=[CH:24][C:25]=2[O:29]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27362715-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

Produkt 1

HCID 6658042110-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-oneAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (262 mg, 1.24 mmol, obtained in example 133, step 3), potassium carbonate (790 mg, 3.72 mmol) and cuprous iodide (354 mg, 1.86 mmol) was added a solution of 5-bromo-2,2-difluoro-benzo[1,3]dioxole (588 mg, 2.48 mmol) in 5 ml toluene under argon. The solution was then degassed by bubbling argon through the mixture for 2 mins after which N—N′-dimethylethylenediamine (266 uL, 2.48 mmol) was added. The sealed tube was closed and the mixture was heated to 110° C. overnight. The reaction mixture was then cooled to room temperature and filtered through a short pad of Celite® using ethyl acetate to wash the mixture through. The solution was then concentrated in vacuo to give a residue which was purified by flash column chromatography (3:7 ethyl acetate heptane) to give the title compound as white solid (350 mg, 75%). MS (m/e): 368.0 [MH+].

Aufarbeitung

  1. customThe solution was then degassed
  2. additionwas added
  3. customThe sealed tube was closed
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. filtrationfiltered through a short pad of Celite®
  6. washto wash the mixture through
  7. concentrationThe solution was then concentrated in vacuo
  8. customto give a residue which
  9. customwas purified by flash column chromatography (3:7 ethyl acetate heptane)

Quellen und Nachweise

ORD-Eintrag
ord-816863bf2a7e4d4ab551257b6d89a0ca
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440710B2

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