Dimethyl Disulfide → ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

HRID 12617

Reaction equation

HRID 12617 reaction equation
CS[S:3][CH3:4].S(Cl)(Cl)(=O)=O.[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:17]([S:3][CH3:4])=[C:16]2[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

6

Reactant 4

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 66738782ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate

Product 1

HCID 68693460ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a chloroform (0.8 mL) solution of dimethyl disulfide (30 mg), sulfuryl chloride (34 mg) was added at −15° C. and the mixture was stirred at −5° C. for 1.5 hours. To the reaction mixture, a chloroform (0.5 mL) solution of the compound prepared in Example 43, namely, ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate (100 mg) was added at −78° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9) to obtain the titled compound having the following physical properties (70 mg).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9)

Sources & evidence

ORD record
ord-89b9fac623f644f58e5b221f3871bc84
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Linked notes

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