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Potassium Iodide → {4-[3-(7-Propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester

HRID 269957
ノート
印刷プレビュー

反応式

HRID 269957 の反応式
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:27]=[CH:26][C:18]4[C:19]([C:22]([F:25])([F:24])[F:23])=[N:20][O:21][C:17]=4[C:16]=3[CH2:28][CH2:29][CH3:30])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:31][O:32][C:33](=[O:36])[CH2:34]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:31][O:32][C:33](=[O:36])[CH2:34][N:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:27]=[CH:26][C:18]4[C:19]([C:22]([F:24])([F:23])[F:25])=[N:20][O:21][C:17]=4[C:16]=3[CH2:28][CH2:29][CH3:30])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 115245536-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole

生成物 1

HCID 11569417{4-[3-(7-Propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester収率 76%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole (0.100 g, 0.24 mmol), methyl-2-bromoacetate (0.109 g, 0.72 mmol), potassium carbonate (0.050 g, 0.36 mmol), potassium iodide (0.008 g, 0.05 mmol), and acetonitrile (15 mL) was stirred and refluxed for 12 hours. The mixture was cooled to room temperature and filtered to remove suspended salts. The solvent was removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was collected, washed with water (2×20 mL) and brine (2×20 mL), and then dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatograph over silica gel using hexane/ethyl acetate (95/5) as an eluant to afford {4-[3-(7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-yloxy)-propoxy]-indol-1-yl}-acetic acid methyl ester (0.089 g, yield: 76%).

後処理

  1. temperaturerefluxed for 12 hours
  2. filtrationfiltered
  3. customto remove
  4. customThe solvent was removed in vacuo
  5. customthe residue partitioned between dichloromethane and water
  6. customThe organic layer was collected
  7. washwashed with water (2×20 mL) and brine (2×20 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was removed
  10. customthe residue was purified by flash chromatograph over silica gel

出典と根拠

ORDレコード
ord-394f7bbd21e94f00a5e6f45824a8d3ac
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07449478B2

反応ノート

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