Trichloroacetonitrile → (+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate

HRID 913843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913843
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([OH:13])[CH3:12])[CH:10]=1)[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:6]=[CH:5]2.[Cl:22][C:23]([Cl:27])([Cl:26])[C:24]#[N:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>ClCCl>[Cl:22][C:23]([Cl:27])([Cl:26])[C:24](=[NH:25])[O:13][CH:11]([C:9]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]2[C:8]=1[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[N:6]=[CH:5]2)[CH3:12]

Komponenten

5

Edukt 3

HCID 11011TrichloroacetonitrileHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 57546085(+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol

Produkt 1

HCID 57546156(+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (±)-1-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol (575 mg, 1.55 mmol) and trichloroacetonitrile (1.55 mL, 15.5 mmol) in dichloromethane (15 mL) at room temperature was added diazabicycloundecene (50 μL, 0.33 mmol). After stirring 30 min, the reaction was concentrated and purified by column chromatography (10% EtOAc/Hex+0.5% Et3N) to give 780 mg (98%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 8.30 (s, 1H), 7.92 (d, J=2.4, 1H), 7.79 (d, J=1.5, 1H), 7.69 (d, J=1.8, 1H), 6.67 (q, J=6.4, 1H), 6.25 (d, J=11.6, 1H), 5.70 (d, J=11.6, 1H), 3.42-3.60 (m, 3H), 1.76 (d, J=6.4, 3H), 1.19 (m, 2H), 0.75-1.02 (m, 2H), -0.06 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 161.2, 135.6, 133.1, 128.0, 127.9, 127.6, 123.2, 114.8, 91.4, 80.2, 72.7, 66.1, 22.5, 17.8, −1.4.

Aufarbeitung

  1. concentrationthe reaction was concentrated
  2. custompurified by column chromatography (10% EtOAc/Hex+0.5% Et3N)
  3. customto give 780 mg (98%) as a colorless film

Quellen und Nachweise

ORD-Eintrag
ord-4c94385a9d654be183223b4721dcfb64
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

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