Potassium Iodide → HCID 68823319、化合物

HRID 751216

反応式

HRID 751216 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[OH:15])[CH:8]=[CH:7]1)[CH3:2].[F:17][C:18]([F:37])([F:36])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:30][CH2:29][CH2:28][C:27]#[C:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][C:18]([F:17])([F:36])[F:37])=[CH:21][CH:22]=2)[CH:8]=[CH:7]1)[CH3:2]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl esterHCID 68821713(7-Hydroxy-indol-1-yl)-acetic acid ethyl ester

生成物 1

HCID 68823319HCID 68823319、化合物収率 16%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A suspension of (7-hydroxy-indol-1-yl)-acetic acid ethyl ester (50 mg, 0.23 mmol), methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester (74 mg, 0.23 mmol; example 9 a]), cesium carbonate (82 mg, 0.25 mmol) and a trace of potassium iodide in acetonitrile (2.5 ml) was stirred for 14 h at ambient temperature and for 4 h at 50° C. The reaction mixture was poured onto 1 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, heptane/AcOEt) to give 16 mg (0.04 mmol, 16%) of the title compound as colorless oil.

後処理

  1. extractionextracted two times with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, heptane/AcOEt)

出典と根拠

ORDレコード
ord-46e817aee03d440dae31dee27ff02f49
出典データセット
uspto-grants-2008_07
特許番号
US07405236B2

関連ノート

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