Sodium hydride → HCID 178494050, Verbindung

HRID 2206036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206036
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[C@H:26]2[CH2:31][CH2:30][C@@H:29]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:28][CH2:27]2)(=O)=O)=CC=1>CN(C=O)C>[Si:33]([O:32][C@H:29]1[CH2:28][CH2:27][C@H:26]([N:4]2[C:5]3[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH3:12])[C:6]=3[C:2]([I:1])=[CH:3]2)[CH2:31][CH2:30]1)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridineHCID 178427786HCID 178427786, Verbindung

Produkt 1

HCID 178494050HCID 178494050, VerbindungAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (0.100 g) in DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 36.5 mg), and the mixture was stirred at room temperature for 1 hr. cis-4-((tert-Butyl(dimethyl)silyl)oxy)cyclohexyl 4-methylbenzenesulfonate (351 mg) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (31.1 mg).

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3284215cec674fef8fbf13b70d037201
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371320B2

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