2-Bromopropane → 5-iodo-1-isopropyl-1H-indazole

HRID 1661456

Reaktionsgleichung

Reaktionsgleichung von HRID 1661456
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH:11](Br)([CH3:13])[CH3:12].[CH3:15][C:16]([O-])(C)[CH3:17].[K+]>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([CH3:13])[CH3:12])[N:6]=[CH:5]2.[I:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH:16]([CH3:17])[CH3:15])[N:7]=2)[CH:3]=1

Komponenten

7

Edukt 3

HCID 63582-BromopropaneHCID 218947395-Iodo-1H-indazoleHCID 23665647Potassium tert-butoxide

Produkt 2

HCID 593398645-iodo-1-isopropyl-1H-indazoleAusbeute 52 %HCID 666878755-iodo-2-isopropyl-2H-indazoleAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-iodo-1H-indazole (488 mg, 2 mmol), isopropyl bromide (244 mg, 2 mmol), and KOtBu (336 mg, 3 mmol) in dry DMF (4 ml) was stirred at room temp. overnight. Then it was diluted with ethyl acetate (50 ml), washed with water (2×50 ml), and dried with Na2SO4. Evaporation of solvent and purification by flash chromatography on silica gel (n-heptane/ethyl acetate) afforded the subtitle compound (298 mg, 52%) along with 5-iodo-2-isopropyl-2H-indazole (227 mg, 40%).

Aufarbeitung

  1. washwashed with water (2×50 ml)
  2. dry with materialdried with Na2SO4
  3. customEvaporation of solvent and purification by flash chromatography on silica gel (n-heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-57c40bcdf2c846aca8d2f0c5815ccbd2
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030340B2

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