2-tert-Butyl-1,1,3,3-tetramethylguanidine → 3-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole

HRID 706701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706701
C(N=C(N(C)C)N(C)C)(C)(C)C.[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[NH:16][N:15]=1.Br.Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>CC#N.O>[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[N:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:15]=1

Komponenten

6

Edukt 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 129138592-(2-Bromoethyl)pyridine hydrobromideHCID 178526562HCID 178526562, Verbindung

Produkt 1

HCID 679763233-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazoleAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Tert-butyl-1,1,3,3-tetramethyl-guanidine (0.48 mL, 2.4 mmol) was added to a mixture of 3-iodo-4-nitro-1H-indazole (0.30 g, 1.0 mmol) and 2-(2-bromoethyl)pyridine hydrobromide (0.30 g, 1.1 mmol) in CH3CN (4 mL). The mixture was stirred at ambient temperature overnight, diluted with H2O (35 mL), stirred for 30 minutes, and then extracted with CHCl3. The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with EtOAc, to provide 3-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole (0.14 mg, 34%) as a solid.

Aufarbeitung

  1. stirringstirred for 30 minutes
  2. extractionextracted with CHCl3
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3518179b6d084d8aae756dee8c6b6544
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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