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Sodium Carbonate → tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate

HRID 41166
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 41166
Br[C:2]1[CH:3]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18].[C:23]([O:27][C:28]([N:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O)=[O:29])([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:22][O:21][C:19]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([C:31]3[N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[CH:34]=[CH:33][CH:32]=3)[CH:3]=1)[O:10][C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:8][C:7]2=[O:18])=[O:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 58234996methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Produkt 1

HCID 86672403tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylateAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred suspension of methyl 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylate (23 g, 62.47 mmol) in DME (300 mL) and water (30 mL) were added 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (14.50 g, 68.72 mmol), Na2CO3 (19.87 g, 187.41 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.877 g, 1.25 mmol). The mixture was degassed with argon and heated to 80° C. for 7 h. Reaction was cooled down and concentrated, the residue was dissolved in 300 mL of DCM and 300 mL of water. The organic phase was decanted, washed with brine then dried over MgSO4, filtered and concentrated to afford a crude compound which was purified on silica, eluting with 80% AcOEt in DCM. The solvents were evaporated to afford tert-butyl 2-(6-(methoxycarbonyl)-2-morpholino-4-oxo-4H-chromen-8-yl)-1H-pyrrole-1-carboxylate (20 g, 70%) as a white powder.

Aufarbeitung

  1. customThe mixture was degassed with argon
  2. customReaction
  3. temperaturewas cooled down
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in 300 mL of DCM
  6. customThe organic phase was decanted
  7. washwashed with brine
  8. dry with materialthen dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a crude compound which
  12. customwas purified on silica
  13. washeluting with 80% AcOEt in DCM
  14. customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-52afd7aa4d6940a3a6e433b0f25069de
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530470B2

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