Trimethylsilyl iodide → 3-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20542
[CH3:1][N:2]([CH3:34])[S:3]([C:6]1[CH:33]=[CH:32][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][O:29]C)[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:8][CH:7]=1)(=[O:5])=[O:4].I[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:34][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][OH:29])[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:32][CH:33]=1)(=[O:4])=[O:5]

Komponenten

5

Edukt 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 115983163-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Produkt 1

HCID 115473993-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (500 mg, 1.0 mmol) in acetonitrile (30 mL) was added iodotrimethylsilane (0.73 mL, 1.0 g, 5.1 mmol) dropwise. The resulting mixture was stirred at RT for 20 hours. Aqueous sodium hydrogen carbonate solution (saturated, 5 mL) was added slowly and the resulting mixture was concentrated under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (50 mL). The organic layers was washed with brine (50 mL), dried (MgSO4) and evaporated to afford the crude product. This was purified by flash chromatography (eluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane) to afford the pure title compound (216 mg, 45%).

Aufarbeitung

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionWater (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (50 mL)
  4. washThe organic layers was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto afford the crude product
  8. customThis was purified by flash chromatography (
  9. washeluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-60a155fcb74746c3abc4c5795b20f29d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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