Sodium hydride → 2-(Trimethylsilyl)ethyl 4-{4-[(1E)-3-(dimethylamino)-3-oxopropen-1-yl]phenyl}isoquinoline-6-carboxylate

HRID 1959957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959957
C(OP([CH2:9][C:10]([N:12]([CH3:14])[CH3:13])=[O:11])(=O)OCC)C.[H-].[Na+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])=[O:36])[CH:33]=3)[CH:28]=[N:27][CH:26]=2)=[CH:21][CH:20]=1)=O.[Cl-].[NH4+]>ClCCl>[CH3:14][N:12]([CH3:13])[C:10](=[O:11])/[CH:9]=[CH:17]/[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:43])[CH3:42])=[O:36])[CH:33]=3)[CH:28]=[N:27][CH:26]=2)=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11127903diethyl N,N-dimethylcarbamoylmethylphosphonateHCID 866619662-(Trimethylsilyl)ethyl 4-(4-formylphenyl)isoquinoline-6-carboxylate

Produkt 1

HCID 667305202-(Trimethylsilyl)ethyl 4-{4-[(1E)-3-(dimethylamino)-3-oxopropen-1-yl]phenyl}isoquinoline-6-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diethyl[2-(dimethylamino)-2-oxoethyl]phosphonate (133 mg, 0.597 mmol) was dissolved in dichloromethane (4 mL), to which 55% sodium hydride (21 mg, 0.48 mmol) was added at 0° C., followed by stirring for 10 minutes. To this solution, 2-(trimethylsilyl)ethyl 4-(4-formylphenyl)isoquinoline-6-carboxylate (150 mg, 0.40 mmol) synthesized in Example 13 (13a) was added, followed by stirring for one hour. To the resulting reaction liquid, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-35:65, V/V) to give the desired title compound (168 mg, yield 95%).

Aufarbeitung

  1. additionwas added at 0° C.
  2. stirringby stirring for one hour
  3. customTo the resulting reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-35:65, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-7ba8a48ef372433d8085016b481eb4a5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410273B2

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