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 1512774ノート

反応式

HRID 1512774 の反応式
[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]

参加物

5

反応物 3

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

生成物 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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
20 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-0634d4b9eef5475fb9f161071756848f
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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