Cesium carbonate → Tert-butyl (3-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-phenyl)-carbamate

HRID 13290

반응식

HRID 13290 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O.[F:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:29]=[CH:30][C:31]=1[OH:32]>C(OCC)(=O)C>[F:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH:29]=[CH:30][C:31]=1[O:32][C:2]1[CH:7]=[N:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 11708410tert-Butyl (3-Fluoro-4-hydroxyphenyl)carbamateHCID 231452295-chloro-2-(methylsulfonyl)Pyridine

생성물 1

HCID 86619205Tert-butyl (3-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-phenyl)-carbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

4.00 g of 5-chloro-2-methanesulfonyl-pyridine and 8.80 g of cesium carbonate were added to an N-methylpyrrolidinone (50 ml) solution of 4.74 g of tert-butyl (3-fluoro-4-hydroxy-phenyl)-carbamate obtained in (step 1), and the reaction liquid was stirred at 100° C. for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound.

후처리

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. washwashed with water and saturated saline in order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
  8. customto obtain the entitled compound

출처 및 근거

ORD 기록
ord-f25b9b9defd24663b180c955f8b5d0f7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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