Potassium Iodide → HCID 68823319, 화합물

HRID 751216

반응식

HRID 751216 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 68823319HCID 68823319, 화합물수율 16%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-46e817aee03d440dae31dee27ff02f49
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405236B2

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