Potassium Carbonate → 5-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole

HRID 706740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706740
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[S:26][C:25]([CH3:27])=[N:24][CH:23]=1>CN(C=O)C.O.CCOC(C)=O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:21][C:22]2[S:26][C:25]([CH3:27])=[N:24][CH:23]=2)[N:3]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 552507865-(Bromomethyl)-2-methyl-1,3-thiazoleHCID 178526562HCID 178526562, Verbindung

Produkt 1

HCID 679761065-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazoleAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-iodo-4-nitro-1H-indazole (441 mg, 1.53 mmol) in anhydrous DMF (3 mL) were added potassium carbonate (422 mg, 3.05 mmol), and 5-(bromomethyl)-2-methylthiazole (440 mg, 2.30 mmol) at ambient temperature and under a nitrogen atmosphere. The resulting mixture was stirred at ambient temperature overnight (about 18 hours). The reaction mixture was diluted with water (10 mL) and EtOAc (20 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The combined organic extracts were concentrated, and the residue subjected to flash liquid chromatography on silica with Hexanes:EtOAc (10:1) as the eluent to afford the desired product (611 mg).

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
  3. concentrationThe combined organic extracts were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-580bce65506544febaeb4232d83d5177
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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