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Sodium bis(trimethylsilyl)amide → 4-[(6-tert-butoxy-5-chloropyridin-3-yl)oxy]-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 2048031
ノート
印刷プレビュー

反応式

HRID 2048031 の反応式
FC1(F)CC(C([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=O)C1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl:24][C:25]1[C:26]([O:39][C:40]2[CH:41]=[N:42][C:43](F)=[C:44]([Cl:46])[CH:45]=2)=[CH:27][C:28]([F:38])=[C:29]([CH:37]=1)[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:31]>C1(C)C=CC=CC=1>[C:9]([O:8][C:43]1[N:42]=[CH:41][C:40]([O:39][C:26]2[C:25]([Cl:24])=[CH:37][C:29]([C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:31])=[C:28]([F:38])[CH:27]=2)=[CH:45][C:44]=1[Cl:46])([CH3:12])([CH3:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 580424375-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamideHCID 58042504Cyclobutanecarboxylic acid, 3,3-difluoro-, 1,1-dimethylethyl ester

生成物 1

HCID 580424094-[(6-tert-butoxy-5-chloropyridin-3-yl)oxy]-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide収率 44.8%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

実験手順

To a solution of tert-butyl 3,3-difluorocyclobutanecarboxylate (Preparation 227, 126 mg, 0.66 mmol) in toluene (2 mL) was added a solution of sodium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (1M solution in THF, 1.6 mL, 1.6 mmol) at 0° C. The resulting solution was stirred for 10 minutes at the same temperature, then 5-chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide (Example 19, 200 mg, 0.50 mmol) was added. The resulting mixture was warmed up to room temperature and stirred for 36 hours. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase was washed with aqueous 1N citric acid solution, then brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product as a yellow oil. The crude product was purified by silica gel column chromatography eluting with 0-100% EtOAc in heptane to give a yellow foam. The foam was triturated with heptane to give the title compound (101 mg, 44%) as a white solid.

後処理

  1. stirringstirred for 36 hours
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with aqueous 1N citric acid solution
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product as a yellow oil
  9. customThe crude product was purified by silica gel column chromatography
  10. washeluting with 0-100% EtOAc in heptane
  11. customto give a yellow foam
  12. customThe foam was triturated with heptane

出典と根拠

ORDレコード
ord-05957889bf644456b36b6e323b1ec333
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592629B2

反応ノート

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