Sodium Chloride → 1,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1H-indazol-4-ylimino)-methyl]-pentan-2-ol

HRID 1443221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443221
[F:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[CH3:22][C:23]1[C:24]([NH2:32])=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[CH:26]2.C1(C)C(C)=CC=CC=1.[Cl-].[Na+]>C(OCC)(=O)C>[F:16][C:13]([F:14])([F:15])[C:10]([CH:11]=[N:32][C:24]1[C:23]([CH3:22])=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[N:27][NH:28]2)([OH:17])[CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[O:20][CH3:21])([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 7237O-XyleneHCID 179890864-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 193544325-Methyl-1H-indazol-4-amine

Produkt 1

HCID 686820761,1,1-Trifluoro-4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1H-indazol-4-ylimino)-methyl]-pentan-2-olAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanal (308 mg, 1.0 mmol) and 5-methyl-1H-indazol-4-ylamine (148 mg, 1.0 mmol) are introduced into 15.0 ml of xylene and mixed with titanium(IV)ethylate (0.42 ml, 2.0 mmol). After 3 hours under reflux, the reaction mixture is allowed to cool to room temperature. After ethyl acetate and saturated sodium chloride solution are added, it is stirred vigorously for 30 minutes at room temperature. The deposited precipitate is suctioned off, the aqueous phase is separated, and the organic phase is dried on sodium sulfate. The purification is carried out by means of chromatography on silica gel with hexane/ethyl acetate (30-40% ethyl acetate). 345 mg (79% of theory) of 1,1,1-trifluoro-4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1H-indazol-4-ylimino)methyl]-pentan-2-ol is obtained.

Aufarbeitung

  1. temperatureAfter 3 hours under reflux
  2. customthe aqueous phase is separated
  3. customthe organic phase is dried on sodium sulfate
  4. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-873a4d70d5a44c94be53f3e60f048514
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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