Sodium Carbonate → 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol

HRID 1399890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399890
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:2]2[C:10]3[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:34]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 867292361-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-olHCID 86729285HCID 86729285, Verbindung

Produkt 1

HCID 867292841-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-olAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (200 mg, 0.611 mmol), 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol (375 mg, 0.916 mmol), Pd(dppf)Cl2 (89 mg, 0.12 mmol) and Na2CO3 (130 mg, 1.22 mmol) in dioxane and H2O was stirred under N2 atmosphere at 100° C. for 3 h. The mixture was extracted with DCM and the combined organic layers dried over Na2SO4 and concentrated in vacuum to give the crude product (265 mg, Yield 82%) which was used without further purification.

Aufarbeitung

  1. extractionThe mixture was extracted with DCM
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cf1550b8bb2742659a48d245f3f3b856
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906900B2

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