Silane, (ethenyloxy)trimethyl- → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal

HRID 563398ノート

反応式

HRID 563398 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)([CH3:19])[CH3:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C[Si](C)(C)[O:23][CH:24]=[CH2:25]>ClCCl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:19])([CH3:18])[CH2:23][CH:24]=[O:25])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 80344Silane, (ethenyloxy)trimethyl-HCID 670058142-(1-(4-fluorophenyl)-1H-indazol-5-yl)propan-2-ol

生成物 1

HCID 866403053-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 2-(1-(4-fluorophenyl)-1H-indazol-5-yl)propan-2-ol (Example 113(d), 200 mg, 0.74 mmol) and trimethyl(vinyloxy)silane (0.5 mL) in anhydrous dichloromethane (1 mL) was added zinc chloride (1M solution in diethyl ether, 2.2 mL, 2.2 mmol) dropwise at 0° C. under argon. The reaction mixture was stirred at rt for 1.5 hr before being quenched by the addition of saturated aqueous ammonium chloride solution (2 mL). The aqueous layer was separated and extracted with ethyl acetate (2×2 mL). The combined organic layers were dried (Na2SO4), concentrated and purified by silica gel flash chromatography to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal as a liquid.

後処理

  1. custombefore being quenched by the addition of saturated aqueous ammonium chloride solution (2 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×2 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-23c79fa6a26148e1849251901563fa1f
出典データセット
uspto-grants-2011_11
特許番号
US08067447B2

反応ノート

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