Sulfoxonium, trimethyl-, iodide (1:1) → Methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate

HRID 1512774Notes

Reaction equation

HRID 1512774 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7][Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:17][C:18]1[CH:19]=[C:20]([C:28]2[O:32][N:31]=[C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[C:37]4[C:41]=3[N:40]([CH3:42])[CH:39]=[C:38]4/[CH:43]=[CH:44]\[C:45]([O:47][CH3:48])=[O:46])[N:29]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26]>CS(C)=O>[CH3:48][O:47][C:45]([CH:44]1[CH2:7][CH:43]1[C:38]1[C:37]2[C:41](=[C:33]([C:30]3[N:29]=[C:28]([C:20]4[CH:21]=[CH:22][C:23]([O:24][CH:25]([CH3:26])[CH3:27])=[C:18]([Cl:17])[CH:19]=4)[O:32][N:31]=3)[CH:34]=[CH:35][CH:36]=2)[N:40]([CH3:42])[CH:39]=1)=[O:46]

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59146121HCID 59146121, compound

Product 1

HCID 67094311Methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of trimethylsulfoxonium iodide (234 mg) in DMSO (3 mL) stirred under nitrogen at 20° C. was added NaHMDS (1.0 mol/L in THF, 1.0 mL) dropwise during 5 mins. The reaction mixture was stirred at this temperature for 15 mins. A solution of methyl (2Z)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-propenoate (D63) (120 mg) in DMSO was added dropwise. After addition was complete, the reaction was stirred at room temperature for 1.5 h, and then warmed to 50° C. for 4 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water, aqueous HCl (2 M) and brine, dried over sodium sulphate and evaporated to afford methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate (D65) (100 mg). MS (ES): C25H24ClN3O4 requires 465. found 466.2 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at this temperature for 15 mins
  2. additionAfter addition
  3. stirringthe reaction was stirred at room temperature for 1.5 h
  4. temperaturewarmed to 50° C. for 4 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
  7. washThe organic phase was washed with water, aqueous HCl (2 M) and brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-0634d4b9eef5475fb9f161071756848f
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…