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Triethylamine → [6-(5-Ethoxymethoxy-benzofuran-2-yl)-2-nitro-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester

HRID 627310
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 627310
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](B(O)O)=[CH:11][C:10]=2[CH:17]=1)[CH3:2].[C:18]([O:22][C:23](=[O:36])[N:24]([C:26]1[C:27]([N+:33]([O-:35])=[O:34])=[N:28][C:29](Br)=[CH:30][CH:31]=1)[CH3:25])([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC>C(O)C.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:18]([O:22][C:23](=[O:36])[N:24]([C:26]1[C:27]([N+:33]([O-:35])=[O:34])=[N:28][C:29]([C:12]2[O:13][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][O:3][CH2:1][CH3:2])=[CH:17][C:10]=3[CH:11]=2)=[CH:30][CH:31]=1)[CH3:25])([CH3:21])([CH3:19])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 461839705-Ethoxymethoxy-benzofuran-2-boronic acidHCID 46855854(6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 46183969[6-(5-Ethoxymethoxy-benzofuran-2-yl)-2-nitro-pyridin-3-yl]-methyl-carbamic acid tert-butyl esterAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a degassed solution of 5-ethoxymethoxy-benzofuran boronic acid (4) (140 mg, 0.593 mmol) in ethanol (10 mL), (6-bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester (7) (151 mg, 0.455 mmol), Pd(PPh3)2Cl2 (42 mg, 0.059 mmol) and Et3N (127 μL, 0.909 mmol) were added. The reaction mixture was stirred at 100° C. for 30 minutes in a microwave reactor. Volatiles were removed under reduced pressure. The residue was diluted with water (15 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash column chromatography using 20% ethyl acetate in hexane. Evaporation of solvent gave title compound 8 (170 mg) as a pale yellow solid.

Aufarbeitung

  1. customVolatiles were removed under reduced pressure
  2. additionThe residue was diluted with water (15 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography
  8. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-94bcb6ea5bce452994c3e6d7a15c6332
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309267B2

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