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Dibutyl sulfide → (+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate

HRID 2099754
ノート
印刷プレビュー

反応式

HRID 2099754 の反応式
[CH2:1](SCCCC)[CH2:2]CC.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Li].[CH3:17][C:18]1[C:26]2[C:22](=[CH:23][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:25]=2)[CH:21]=[C:20]([CH2:35][CH:36]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:19]=1>CCOCC>[CH2:1]([C:13]1[CH:14]=[CH:15][N:10]=[C:11]([CH:36]([CH2:35][C:20]2[CH:19]=[C:18]([CH3:17])[C:26]3[C:22](=[CH:23][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[N:25]=3)[CH:21]=2)[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:12]=1)[CH3:2]
参加物反応条件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 11002Dibutyl sulfideHCID 69069206Ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoateHCID 178506720HCID 178506720、化合物

生成物 1

HCID 57794570(+/-)-Ethyl 3-(4-ethylpyridin-2-yl)-4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)butanoate収率 44%

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒
2 回

反応条件

温度
0 °C

実験手順

To a 50-mL oven-dried flask was added di-n-butylsulfide (244 mg, 1.665 mmol, 4.4 equiv) and cuprous iodide (159 mg, 0.832 mmol, 2.2 equiv) under nitrogen. Anhydrous ether (1.2 mL) was added and the suspension was cooled to 0° C. before the solution of 2-pyridinyl lithium was added via canuula. A yellowish brown precipitate was formed. After stirring at 0° C. for 20 min, the cooling bath was removed and ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoate (141.7 mg, 0.378 mmol, 1.0 equiv.) in anhydrous ether (1.2 mL) was added via syringe. The solution was stirred at room temperature for 1 h. The reaction mixture was then partitioned between an aqueous ammonium hydroxide/ammonium chloride solution and ethyl acetate (upon shaking, the solids gradually dissolved to a give blue aqueous solution). The layers were separated and the organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography (5% methanol in methylene chloride) afforded the desired product (80 mg, 44%) which was carried on without farther purification. MS (ESI) 482 (MH)+.

後処理

  1. customTo a 50-mL oven-dried flask
  2. additionwas added via canuula
  3. customA yellowish brown precipitate was formed
  4. customthe cooling bath was removed
  5. stirringThe solution was stirred at room temperature for 1 h
  6. customThe reaction mixture was then partitioned between an aqueous ammonium hydroxide/ammonium chloride solution and ethyl acetate (
  7. stirringupon shaking
  8. dissolutionthe solids gradually dissolved to a give blue aqueous solution)
  9. customThe layers were separated
  10. washthe organic layer was washed with water, brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1cd2ae38c71e4127a4e4d8968a47d2eb
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07569578B2

反応ノート

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