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CAS No. : | 166882-70-8 | MDL No. : | |
Formula : | C19H21NO3S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 375.50 | Pubchem ID : | - |
Synonyms : |
ZD 4407
|
Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In dimethyl sulfoxide; | EXAMPLE 28 Potassium tert-butoxide (1.66 g) was added portionwise to a stirred solution of (2S,4R)-4-hydroxy-4-(2-mercaptothien-4-yl)-2methyltetrahydropyran (3.15 g) in DMSO (25 ml) and the mixture was stirred at ambient temperature for 5 minutes. 5-Bromo-1-methylindolin2-one (3.71 g) and tetrakis(triphenylphosphine)palladium(O) (1.59 g) were added and the mixture was heated to 100 C. for 75 minutes. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and a mixture of ice and water. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p. 40-60 C.) and ethyl acetate as eluent. The material so obtained was further purified by column chromatography using a 5:1 mixture of methylene chloride and acetone as eluent. There was thus obtained (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thien-4-yl]tetrahydropyran (2.45 g, 48%), m.p. 125-127 C. (recrystallized from diethyl ether containing a few drops of methylene chloride) and m.p. 129.5-130.5 C. after a further recrystallisation from ethyl acetate; NMR Spectrum: 1.15 (d, 3H), 1.70 (m, 4H), 1.95 (m, 1H), 3.12 (s, 3H), 3.40 (s, 2H), 3.85 (m, 3H), 6.68 (d, 1H), 7.18 (m, 3H), 7.27 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: triphenylphosphine / water; dichloromethane / 0.5 h / Reflux; Inert atmosphere 2.1: dichloromethane / 2 h / Reflux; Inert atmosphere 3.1: potassium cyanide; sodium carbonate / toluene; water / 1 h / pH 10 / Inert atmosphere 4.1: iodine / dichloromethane / 1 h / Reflux; Inert atmosphere 5.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 12 °C / Inert atmosphere 5.2: Inert atmosphere | ||
Multi-step reaction with 6 steps 1.1: triphenylphosphine / water; dichloromethane / 0.5 h / Reflux; Inert atmosphere 2.1: dichloromethane / 2 h / Reflux; Inert atmosphere 3.1: potassium cyanide; sodium carbonate / toluene; water / 1 h / pH 10 / Inert atmosphere 4.1: iodine / dichloromethane / 1 h / Reflux; Inert atmosphere 5.1: triethylamine / toluene / 0.25 h / -54 - -50 °C / Inert atmosphere 6.1: sulfuric acid / toluene; acetonitrile; water / 65 h / 20 - 30 °C / Inert atmosphere; Large scale 6.2: 85 °C / Inert atmosphere; Large scale |