Sulfoxonium, trimethyl-, iodide (1:1) → HCID 58222469, compound

HRID 1512773Notes

Reaction equation

HRID 1512773 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][CH2:48][CH3:49])=[O:46])[N:29]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26]>CS(C)=O>[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[C@@H:43]3[CH2:7][C@H:44]3[C:45]([O:47][CH2:48][CH3:49])=[O:46])[N:29]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59146049HCID 59146049, compound

Product 1

HCID 58222469HCID 58222469, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of trimethylsulfoxonium iodide (132 mg) in DMSO (3 mL) stirred under nitrogen at 20° C. was added NaHMDS (1.0 mol/L in THF, 0.6 mL) dropwise during 5 mins. The reaction mixture was stirred at this temperature for 15 mins. A solution of ethyl (2E)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-propenoate (D62) (140 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 2 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 ethyl (1R,2R)-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate (D64) (80 mg). MS (ES): C26H26ClN3O4 requires 479. found 480.2 (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 2 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-0ce414a9fccf4a60a49a23c11799d6a3
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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