Dimethylformamide → N-(3'-Benzyloxy-5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide

HRID 17309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17309
CN(C)C=O.[C:6]([C:8]1[C:13]([CH3:14])=[C:12](I)[C:11]([F:16])=[C:10]([O:17][CH3:18])[C:9]=1[NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])#[N:7].[CH2:26]([O:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH2:26]([O:33][C:34]1[CH:39]=[C:38]([C:12]2[C:13]([CH3:14])=[C:8]([C:6]#[N:7])[C:9]([NH:19][C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[C:10]([O:17][CH3:18])[C:11]=2[F:16])[CH:37]=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 27343133-Benzyloxy-phenylboronic acidHCID 86630809N-(2-Cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 86630821N-(3'-Benzyloxy-5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (287 mg, 249 μmol) was added to an N,N-dimethylformamide (16.5 ml) suspension of N-(2-cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2,2-trifluoroacetamide (I-35) (500 mg, 1.24 mmol), 3-benzyloxyphenylboronic acid (425 mg, 1.87 mmol), potassium phosphate n-hydrate (74-78%, 713 mg, 2.49 mmol), followed by stirring at 95° C. for 5.5 hours. The reaction liquid was cooled, then ethyl acetate (100 ml) was added, followed by washing with saturated brine (50 ml×3), drying over anhydrous magnesium sulfate, concentration under reduced pressure. The residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1), (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (415 mg, 73%) as a yellow solid.

Aufarbeitung

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. washby washing with saturated brine (50 ml×3)
  4. dry with materialdrying over anhydrous magnesium sulfate, concentration under reduced pressure
  5. customThe residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1), (n-hexane:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-0cdab517b6264e6e8af8ce52228e65fe
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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