Dimethylformamide → HCID 21082195, Verbindung

HRID 1724048Notizen

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-b9dc677255e147afaffc7b53b5e7b2fb
Quelldatensatz: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07485652B2

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