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Water → tert-Butyl 4-(2-(2-chloropyridin-4-yloxy)ethyl)naphthalen-1-ylcarbamate

HRID 2069039
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2069039
[OH:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1.[H-].[Na+].[Cl:24][C:25]1[CH:30]=[C:29](F)[CH:28]=[CH:27][N:26]=1.O>CN(C=O)C>[Cl:24][C:25]1[CH:30]=[C:29]([O:1][CH2:2][CH2:3][C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:6][CH:5]=2)[CH:28]=[CH:27][N:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27827922-Chloro-4-fluoropyridineHCID 68313879tert-Butyl 4-(2-hydroxyethyl)naphthalen-1-ylcarbamate

Produkt 1

HCID 86659922tert-Butyl 4-(2-(2-chloropyridin-4-yloxy)ethyl)naphthalen-1-ylcarbamateAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

To a degassed solution of tert-butyl 4-(2-hydroxyethyl)naphthalen-1-ylcarbamate (32) (0.64 g, 2.23 mmol) in DMF (10 mL) was added sodium hydride (0.267 g, 60% dispersion in mineral oil, 6.68 mmol) under nitrogen at 0° C. The solution was warmed to RT and was stirred for 30 min and then cooled to 0° C. To this mixture was added a solution of 2-chloro-4-fluoro-pyridine (0.381 g, 2.90 mmol) in DMF (5.0 mL) and the reaction mixture was warmed to RT and stirred for 16 hr. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine (3×), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 0-40% ethyl acetate in isohexane, gradient elution) to afford the title compound (33) (0.67 g, 75%); m/z 399 (M+H)+, (ES+).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. temperaturethe reaction mixture was warmed to RT
  3. stirringstirred for 16 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with brine (3×)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography (SiO2, 0-40% ethyl acetate in isohexane, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-bea0b31461f14fba9bfa6d992a63b2ff
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299073B2

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