Sodium hydride → N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide

HRID 1477864ノート

反応式

HRID 1477864 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([N:32]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[N:24]2)([CH2:21][CH3:22])/[CH:17]=[CH:18]/[C:19]#[N:20])=[CH:12][CH:11]=1>CS(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([N:32]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:42])[CH3:43])[S:33]([CH3:36])(=[O:34])=[O:35])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[N:24]2)([CH:17]2[CH2:4][CH:18]2[C:19]#[N:20])[CH2:21][CH3:22])=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86705042(E)-N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-en-3-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide

生成物 1

HCID 70563960N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

A suspension of NaH (22 mg) in anhydrous DMSO (0.9 mL) was added trimethylsulfoxonium iodide (128 mg) at 0° C. and the mixture was stirred at rt for 3 h until the solution became clear. Then was added the solution of (E)-N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-en-3-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide (42 mg) in anhydrous DMSO (0.1 mL) and the reaction mixture was stirred at 70° C. for 16 h. The solution was quenched with saturated NH4Cl solution, extracted with ethyl acetate (15 mL). The organic layer was washed with brine, dried over dry sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=4/1) to afford the title compound as a white solid. LC/MS m/z=559.2 [M+H]+.

後処理

  1. stirringthe reaction mixture was stirred at 70° C. for 16 h
  2. customThe solution was quenched with saturated NH4Cl solution
  3. extractionextracted with ethyl acetate (15 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over dry sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (PE/EA=4/1)

出典と根拠

ORDレコード
ord-66ff165440754d1383d9a27240870683
出典データセット
uspto-grants-2016_08
特許番号
US09403807B2

反応ノート

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