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

Cesium carbonate → 6-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1961477
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:24])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19](I)=[CH:18][N:17]=3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O-:30])([O-])=O.[Cs+].[Cs+].CC1C=N[C:37]2[C:46](C=1C)=[CH:45][CH:44]=[C:43]1[C:38]=2N=CC(C)=C1C>C(O)C1C=CC=CC=1.[Cu]I>[CH2:27]([O:30][C:19]1[CH:20]=[C:21]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH3:24])[C:13]([C:11]([NH:10][CH2:9][C:8]1[CH:25]=[CH:26][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)=[O:12])=[CH:22]2)[C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:38]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 66746137N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide

Produkt 1

HCID 667454906-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamideAusbeute 235,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 244Benzyl AlcoholLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide (135 mg, 0.30 mmol), Cs2CO3 (191.5 mg, 0.6 mmol), CuI (5.6 mg, 0.03 mmol) and 3,4,7,8-tetramethyl-1,10-phenantroline (14.0 mg, 0.06 mmol)) suspended in benzyl alcohol (4.5 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 120° C. overnight. The mixture was allowed to cool. CH2Cl2 was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3) yielding 62 mg of the title compound (47%).

Aufarbeitung

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the suspension for 5 min
  3. customThe tube was sealed
  4. temperatureto cool
  5. additionCH2Cl2 was added
  6. washthe mixture washed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3)

Quellen und Nachweise

ORD-Eintrag
ord-6d277d7471d1496ab58ea35c98806e13
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08415333B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion