Potassium Iodide → [6-[5-(4-Trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl]-acetic acid tert-butyl ester

HRID 915384

反応式

HRID 915384 の反応式
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:20][C:21]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[NH:23][N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:20][C:21]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=4)[NH:23][N:22]=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetateHCID 1785061113-Chloromethyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole

生成物 1

HCID 178451203[6-[5-(4-Trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-indol-1-yl]-acetic acid tert-butyl ester収率 7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (37 mg, 0.15 mmol), 3-chloromethyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole (43 mg, 0.16 mmol), cesium carbonate (54 mg, 0.16 mmol) and a trace of potassium iodide were suspended in N,N-dimethylformamide (4 ml). The suspension was stirred at ambient temperature for 14 h and for 4 h at 80° C. The solvent was evaporated under reduced pressure and the residue dissolved in 1 N HCl/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed two times with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 5 mg (10 μmol, 7%) of the title compound as orange oil.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in 1 N HCl/ice water 1/1
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted two times with ethyl acetate
  5. washThe combined organic layers were washed two times with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

出典と根拠

ORDレコード
ord-9ed5a382e2e74487b457e32e74dee025
出典データセット
uspto-grants-2007_09
特許番号
US07265149B2

関連ノート

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