Sodium Carbonate → di-tert-butyl [6'-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

HRID 594859

Reaktionsgleichung

Reaktionsgleichung von HRID 594859
Br[C:2]1[CH:3]=[C:4]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][C:25]1([CH2:28][O:27][CH2:26]1)[C:5]12[CH2:9][O:8][C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:6]1.CC1(C)C(C)(C)OB([C:42]2[CH2:43][CH2:44][O:45][CH2:46][CH:47]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]([O:13][C:11]([N:10]([C:7]1[O:8][CH2:9][C:5]2([N:6]=1)[C:25]1([CH2:26][O:27][CH2:28]1)[CH2:29][O:30][C:31]1[C:4]2=[CH:3][C:2]([C:42]2[CH2:47][CH2:46][O:45][CH2:44][CH:43]=2)=[CH:33][CH:32]=1)[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[O:12])([CH3:16])([CH3:15])[CH3:17]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86724239Di-tert-butyl (6'-bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)imidodicarbonate

Produkt 1

HCID 86724255di-tert-butyl [6'-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of di-tert-butyl (6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)imidodicarbonate (300 mg, 0.571 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (360 mg, 1.71 mmol), bis(triphenylphosphine)palladium(II) dichloride (40.1 mg, 0.057 mmol) and Na2CO3 (182 mg, 1.71 mmol) in dioxane (3.6 mL) and water (0.9 mL) was stirred for 1 hour at 100° C. The mixture was cooled down to ambient temperature and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, diluted with hexane, and filtered through silica gel pad (eluted with 50% EtOAc in hexane). The filtrate was concentrated at reduced pressure to give crude di-tert-butyl[6′-(3,6-dihydro-2H-pyran-4-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate which was used for the next reaction without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled down to ambient temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. additiondiluted with hexane
  6. filtrationfiltered through silica gel pad (eluted with 50% EtOAc in hexane)
  7. concentrationThe filtrate was concentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-294ec41c494248e4b80280aa176b52fb
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242973B2

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