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Sodium Bicarbonate → N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide

HRID 1641570
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641570
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)=[CH:4][CH:3]=1.[CH:22]([C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])O.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:22]([C:24]1[S:28][C:27]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]3([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:26][CH:25]=1)=[O:23]
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Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27734305-Formyl-2-thiopheneboronic acidHCID 46202882N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

Produkt 1

HCID 57624621N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamideAusbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixed solution of N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (1.07 g) of Reference Example 5, 5-formyl-2-thiopheneboronic acid (0.56 g), sodium hydrogen carbonate (1.51 g), palladium(II) acetate (33.7 mg) and 2-(di-t-butylphosphino)biphenyl (89.5 mg) in 1,2-dimethoxyethane (12 mL)-water (4 mL) was stirred at 65° C. for 9 hr under a nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.25 g) as brown crystals.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2a17d82e6e78402c8ea7b64e743f3c12
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114902B2

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