StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → tert-butyl 4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1749960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1749960
I[C:2]1[C:10]2[O:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].CC1(C)C(C)(C)OB([C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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>[CH3:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[CH2:8][O:9][C:10]=2[C:2]=1[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 712788737-iodo-6-methoxybenzofuran-3(2H)-one

Produkt 1

HCID 71278594tert-butyl 4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-5,6-dihydropyridine-1(2H)-carboxylateAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A solution of 7-iodo-6-methoxybenzofuran-3(2H)-one (0.100 g, 0.345 mmol) synthesized in Example B46, Step 2 in 1,4-dioxane (6 mL) was added with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.107 g, 0.345 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.0252 g, 0.0345 mmol) and 2 M aqueous sodium carbonate (0.515 mL, 1.03 mmol), and the mixture was stirred at 150° C. for 30 minutes under irradiation of microwaves. The reaction mixture was poured into water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was subjected to silica gel column chromatography (hexane/ethyl acetate). The resulting crude product was purified again by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl 4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.0562 g, 47%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting crude product was purified again by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b9d456f6d49b48cfa286ac2c6b500024
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156827B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion