N-Iodosuccinimide → (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

HRID 589201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589201
[CH3:1][Si:2]([CH3:41])([CH3:40])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1.C1C(=O)N([I:49])C(=O)C1>CC#N>[CH3:39][Si:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][O:33][CH2:32][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:40])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:49])=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 67294324(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

Produkt 1

HCID 67294877(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate (6.32 g, 10.5 mmol, preparation described previously) in CH3CN (50 mL) was added NIS (2.60 g, 11.5 mmol). The resulting solution was stirred at it for 1 h. The reaction quenched with Na2SO3 and CH3CN was evaporated. The aqueous residue was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc) to afford the titled compound as a pale yellow oil (6.94 g).

Aufarbeitung

  1. customThe reaction quenched with Na2SO3 and CH3CN
  2. customwas evaporated
  3. extractionThe aqueous residue was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-de0037525a214c42bd6ff39215c6a140
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227971B2

Notizen zur Reaktion

Wird geladen…