Binap, (A+-)- → 2-{3-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}ethanol

HRID 2374897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374897
Cl.[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH2:12])=[N:7]2.Br[C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][OH:28])[CH:23]=[CH:24][CH:25]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:2][C:3]1[N:4]=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:6]2[C:11]=1[CH:10]=[N:9][C:8]([NH:12][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][OH:28])[CH:23]=[CH:24][CH:25]=1)=[N:7]2

Komponenten

7

Edukt 4

HCID 634876Binap, (A+-)-HCID 27340902-(3-Bromophenyl)ethan-1-olHCID 23676156Sodium t-butoxideHCID 688705435-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride

Produkt 1

HCID 112448862-{3-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}ethanolAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a mixture of 5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine hydrochloride (0.026 g, 0.10 mmol), 2-(3-bromophenyl)ethanol (0.022 g, 0.11 mmol), tris(dibenzylideneacetone)dipalladium (2.7 mg, 0.0030 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (5.6 mg, 0.0090 mmol) and sodium t-butoxide (0.025 g, 0.23 mmol) was added dioxane (1 mL). The solution was heated with microwave radiation to 160° C. for 15 minutes. After cooling to room temperature, the solution was filtered, and silica gel (1 g) was added, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexanes (50:50) to ethyl acetate:hexanes (100:0) using a RediSep silica gel cartridge (4 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give 2-{3-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}ethanol (0.0097 g) as a yellow solid. 1H NMR (CDCl3): δ8.75 (s, 1H), 8.51-8.45 (m, 2H), 7.74 (s, 1H), 7.56-7.26 (m, 5H), 7.04-6.95 (m, 2H), 3.91 (t, J=6.4 Hz, 2H), 2.92 (t, J=6.4 Hz, 2H), 2.59 (s, 3H). MS m/z 346 (M+1).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solution was filtered
  3. additionsilica gel (1 g) was added
  4. customfollowed by evaporation of the volatiles under reduced pressure
  5. washsubjected to a gradient elution
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fd75e09d93024ca6b012c156720fa2a8
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462614B2

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