Sodium Bicarbonate → HCID 22646584, Verbindung

HRID 393601

Reaktionsgleichung

Reaktionsgleichung von HRID 393601
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([OH:38])[CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>CS(C)=O.O>[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([CH:37]=1)[O:38][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 219910495-Benzyloxy-2-fluoro-4-methylphenolHCID 22646522HCID 22646522, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 22646584HCID 22646584, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

4-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline (187 mg, 0.71 mmol), (prepared as described for the starting material in Example 1 but with an aqueous sodium hydrogen carbonate work up), was added to a solution of 5-benzyloxy-2-fluoro-4-methylphenol (248 mg, 1 mmol), (prepared as described for the starting material in Example 3), and potassium t-butoxide (120 mg, 1 mmol) in DMSO (5 ml) and the mixture then heated at 160° C. for 1.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/ethyl acetate (55/45) followed by preparative reverse-phase HPLC eluting with aqueous ammonium carbonate (2 g/1, adjusted to pH7 with carbon dioxide) and methanol (20/80) to give 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline (204 mg, 63%).

Aufarbeitung

  1. custom(prepared
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/ethyl acetate (55/45)
  9. washeluting with aqueous ammonium carbonate (2 g/1, adjusted to pH7 with carbon dioxide) and methanol (20/80)

Quellen und Nachweise

ORD-Eintrag
ord-694d6787e78e4946aa91d24d25588844
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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