Potassium Carbonate → N-(sec-butylsulfonyl)-4-[(5-chloro-6-methoxypyridin-3-yl)oxy]-2,5-difluorobenzamide

HRID 2048016노트

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HRID 2048016 반응식
C(=O)([O-])[O-].[K+].[K+].[CH:7]([S:11]([NH:14][C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[C:19](F)=[CH:18][C:17]=1[F:24])(=[O:13])=[O:12])([CH2:9][CH3:10])[CH3:8].[Cl:26][C:27]1[CH:28]=[C:29]([OH:35])[CH:30]=[N:31][C:32]=1[O:33][CH3:34]>CS(C)=O.O>[CH:7]([S:11]([NH:14][C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[C:19]([O:35][C:29]2[CH:30]=[N:31][C:32]([O:33][CH3:34])=[C:27]([Cl:26])[CH:28]=2)=[CH:18][C:17]=1[F:24])(=[O:13])=[O:12])([CH2:9][CH3:10])[CH3:8]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 58042392N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamideHCID 666673833-Chloro-5-hydroxy-2-methoxypyridine

생성물 1

HCID 58042384N-(sec-butylsulfonyl)-4-[(5-chloro-6-methoxypyridin-3-yl)oxy]-2,5-difluorobenzamide수율 52.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

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온도
90 °C

실험 절차

Potassium carbonate (0.140 g, 1.01 mmol) was added to a stirred solution of N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamide (Preparation 68, 0.090 g, 0.30 mmol) in DMSO (1 mL). After 10 minutes a solution of 5-chloro-6-methoxypyridin-3-ol (Preparation 77, 0.088 g, 0.51 mmol) in DMSO (2 mL) was added at room temperature. The mixture was heated at 90° C. for 72 hours. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (3×25 mL). The combined organics were washed with water (25 mL), dried over magnesium sulfate, filtered, evaporated in vacuo. The resulting crude product was purified by silica gel chromatography eluting with 0 to 66% EtOAc in heptane to yield the title compound (0.068 g):

후처리

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined organics were washed with water (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting crude product was purified by silica gel chromatography
  7. washeluting with 0 to 66% EtOAc in heptane

출처 및 근거

ORD 기록
ord-86492491a40b49ce90fd01bffc4fd302
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592629B2

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