Dimethylformamide → HCID 24765407, Verbindung

HRID 1255124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255124
Br[C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]2[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])=[N:13][C:12]=2[CH3:27])[CH:3]=1.[CH3:28][N:29](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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:28]([C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]2[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])=[N:13][C:12]=2[CH3:27])[CH:3]=1)#[N:29]

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 24765405N-(5-(7-Bromobenzo[d][1,3]dioxol-5-yl)-4-methylthiazol-2-yl)-2,6-difluorobenzamide

Produkt 1

HCID 24765407HCID 24765407, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A degassed mixture of Compound 56 (80 mg, 0.18 mmol), zinc cyanide (26 mg, 0.22 mmol) and tetrakis(triphenylphosphine)palladium (20.0 mg, 0.017 mmol) in DMF (2.0 mL) was heated to 100° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate. The mixture was washed with a solution of saturated NaHCO3 then with brine, dried (Na2SO4), filtered and concentrated. The residue was purified on silica to provide Compound 58 (55 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washThe mixture was washed with a solution of saturated NaHCO3
  3. dry with materialwith brine, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica

Quellen und Nachweise

ORD-Eintrag
ord-ba6a557094f04c3688ab46c12cb7dc7f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455658B2

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