Dimethylformamide → HCID 21082195, Verbindung

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=4)[CH:16]=[C:15]3[CH3:33])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.CN([CH:38]=[O:39])C.O=P(Cl)(Cl)Cl>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:34])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:24]([F:26])([F:27])[F:25])[C:28]([F:29])([F:30])[F:31])=[CH:20][CH:21]=4)[C:16]([CH:38]=[O:39])=[C:15]3[CH3:33])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 200 mg (0.4 mmol) of 2-{1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 12) in 2 mL of dichloroethane was treated with 0.06 mL (0.8 mmol) of DMF and cooled to 0° C. After addition of 0.04 mL (0.44 mmol) of POCl3 the mixture was allowed to reach RT and stirred for an additional hour. Distribution of the mixture between Et2O and H2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 1:2 yielded 110 mg (52%) of 1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-3-carbaldehyde, light brown solid, MS: 531 (MH+).

Aufarbeitung

customto reach RT
dry with materialDistribution of the mixture between Et2O and H2O, drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with n-heptane/EtOAc 1:2

Quellen und Nachweise

ORD-Eintrag: ord-fd4ce9770e184784aff745eb5b4465c8
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07173048B2

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