Potassium Carbonate → HCID 76756296, Verbindung

HRID 1949460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949460
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]5[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[N:19][C:18]4=[O:29])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:32]([F:35])([F:34])[F:33])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44][F:45]>C(#N)C>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]5[CH2:28][CH2:27][CH2:26][N:25]([CH2:43][CH2:44][F:45])[CH2:24][CH2:23]5)=[N:19][C:18]4=[O:29])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:32]([F:35])([F:34])[F:33])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 67240905HCID 67240905, Verbindung

Produkt 1

HCID 76756296HCID 76756296, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-[1,4]diazepan-1-yl-thiazol-4-one (0.016 g, 0.03 mmol) in acetonitrile (1.5 mL) was treated with potassium carbonate (0.022 g, 0.15 mmol) and 1-bromo-2-fluoro-ethane (0.04 g, 0.3 mmol). Reaction mixture was stirred at 70° C. for 18 hours and the solvent evaporated in vacuo. The residue was partitioned between dichloromethane and water. The dichloromethane layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (5% methanol in dichloromethane) to yield the title compound (17 mg, 100%).

Aufarbeitung

  1. customReaction mixture
  2. customthe solvent evaporated in vacuo
  3. customThe residue was partitioned between dichloromethane and water
  4. washThe dichloromethane layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto yield a crude solid
  9. customThe crude solid was purified via flash chromatography (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-58a6c073f4d744f497338b49cd1e1b01
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399681B2

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