Potassium Carbonate → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynylamino]-indol-1-yl}-acetic acid ethyl ester

HRID 751208

반응식

HRID 751208 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[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-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][CH2:30][CH2:29][CH2:28][C:27]#[C:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:17])([F:36])[F:37])=[CH:21][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl esterHCID 16731704Ethyl 2-(6-amino-1H-indol-1-yl)acetate

생성물 1

HCID 68823310{6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynylamino]-indol-1-yl}-acetic acid ethyl ester수율 15%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A suspension of (6-amino-indol-1-yl)-acetic acid ethyl ester (50 mg, 0.23 mmol, WO 2003041714 A1), methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester (148 mg, 0.46 mmol) and potassium carbonate (63 mg, 0.46 mmol) in DMF (1 ml) was stirred for 3 h at ambient temperature and for 14 h at 70° C. The reaction mixture was poured onto ethyl acetate/ice water 1/1, the layers were separated and the aqueous layer was 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 (0.03 mmol, 15%) of the title compound as yellow oil.

후처리

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

출처 및 근거

ORD 기록
ord-cae5d914e0fb4d66935730977703649c
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405236B2

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