Cesium carbonate → HCID 68699922, 화합물

HRID 1990817노트

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HRID 1990817 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1.[F:15][C:16]([F:20])([F:19])[CH2:17]I.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH2:17][C:16]([F:20])([F:19])[F:15])[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1

참가 물질

4

반응물 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 15788544Methyl 3-ethoxy-5-hydroxybenzoate

생성물 1

HCID 68699922HCID 68699922, 화합물수율 42%

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온도
130 °C

실험 절차

A mixture of 3-ethoxy-5-hydroxy-benzoic acid methyl ester (1.5 g, 7.65 mmol, 1.0 equiv; prepared as described in WO 99/05123 A1, Astra Pharmaceuticals Ltd.), 2,2,2-trifluoroethyl iodide (2.25 mL, 4.82 g, 22.94 mmol, 3.0 equiv) and cesium carbonate (4.98 g, 15.29 mmol, 2.0 equiv) was heated to 130° C. under microwave irradiation for 20 min. The crude reaction mixture was filtered over Hyflo Super Cel and extracted with dichloromethane (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified by flash column chromatography on silica eluting with a gradient of heptane/dichloromethane (1:1→0:1) yielding 0.89 g (42%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.35 (t, J=7.0 Hz, 3H), 3.84 (s, 3H), 4.00 (q, J=7.0 Hz, 2H), 4.30 (q, J=8.1 Hz, 2H), 6.62-6.63 (m, 1H), 7.10-7.11 (m, 1H), 7.19-7.21 (m, 1H). MS (ISP): 279.0 [M+H]+.

후처리

  1. customThe crude reaction mixture
  2. filtrationwas filtered over Hyflo Super Cel
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe solvent removed by evaporation under reduced pressure
  6. customthe crude material purified by flash column chromatography on silica eluting with a gradient of heptane/dichloromethane (1:1→0:1)

출처 및 근거

ORD 기록
ord-fea9bde581e84dd1a48f522a208e135e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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