Water → HCID 178504257, Verbindung

HRID 929157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929157
[S-2].[Na+].[Na+].[C:4]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([S:27](C)(=O)=O)[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]3=[CH:12][C:11]=2[Cl:31])=[CH:6][CH:5]=1.O>CN(C=O)C>[C:4]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]3[N:16]=[C:17]([SH:27])[N:18]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]3=[CH:12][C:11]=2[Cl:31])=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14804Sodium SulfideHCID 682826082-[[6-Chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane

Produkt 1

HCID 178504257HCID 178504257, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium sulfide (65.6 mg, 0.840 mmol) was added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazo[4,5-b]pyridine (144 mg, 0.280 mmol) in DMF (2 ml) and the mixture was stirred at room temperature for 3 h. Water (30 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic fractions were washed with brine (saturated, 30 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage™ 25S, eluting with 0-30% EtOAc/hexane to give title compound. LC-MS: calculated for C24H26ClN3OSSi 467.13 observed m/e: 468.12 (M+H)+ (Rt 1.38/2 min).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic fractions were washed with brine (saturated, 30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel Biotage™ 25S
  7. washeluting with 0-30% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ef2da9babdda4525892ab5c2c437965a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290517B2

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