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Sodium hydride → methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate

HRID 1427232
ノート
印刷プレビュー

反応式

HRID 1427232 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16]2)([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16]2)([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 57524868methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indazol-1-yl)butanoate

生成物 1

HCID 70565947methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

A solution of methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indazol-1-yl)butanoate (500 mg, 1.19 mmol) in dry THF (8 mL) was treated by NaH (95 mg, 2.38 mmol, 60% in oil) at 0° C. for 30 min, then was added (2-(chloromethoxy)ethyl)trimethylsilane (295 mg, 1.78 mmol) dropwise. The mixture was stirred at room temperature for 2 h. The solution was quenched with saturated NH4Cl solution, and extracted with ethyl acetate (30 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=6/1) to afford the title compound as a pale yellow solid. LC/MS m/z=551.8 [M+H]+.

後処理

  1. customThe solution was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over dry sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=6/1)

出典と根拠

ORDレコード
ord-414430b223464a1b9bb05138ecdbb89e
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933113B2

反応ノート

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