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

HRID 2048016ノート

反応式

HRID 2048016 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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):

後処理

  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

出典と根拠

ORDレコード
ord-86492491a40b49ce90fd01bffc4fd302
出典データセット
uspto-grants-2013_11
特許番号
US08592629B2

反応ノート

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