1,1'-Carbonyldiimidazole → 5-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid cyclobutyl ester

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Reaktionsgleichung

[F:1][C:2]([F:25])([F:24])[C:3]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1)[OH:4].[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].[CH:38]1([OH:42])[CH2:41][CH2:40][CH2:39]1>N1C=CC=CC=1>[CH:38]1([O:42][C:26]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([C:3]([C:5]4[C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[N:7]([CH3:14])[CH:6]=4)([OH:4])[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=3)[CH:18]=[N:19]2)=[O:27])[CH2:41][CH2:40][CH2:39]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.142 mmol) and carbonyldiimidazole (0.185 mmol) in 1 mL of pyridine was heated at 80° C. for 10 hours, cooled to room temperature, and cyclobutanol (1.4 mmol) was added. The mixture was stirred overnight. The volatiles were removed and the residue purified by flash silica gel chromatography using 33% ethyl acetate in hexanes. The product-rich fractions were concentrated in vacuo to provide 0.076 mmol of the desired compound, m.p. 82° C.-84° C.

Aufarbeitung

temperaturecooled to room temperature
customThe volatiles were removed
customthe residue purified by flash silica gel chromatography
concentrationThe product-rich fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-54aebfaef37247b9a8c92cfd356e3117
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08658637B2

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