3-(Trifluoromethyl)benzenesulfonyl chloride → N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide

HRID 419022

反応式

HRID 419022 の反応式
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1>[Br:1][C:2]1[C:7]([NH:8][S:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:22])[F:23])[CH:13]=2)(=[O:20])=[O:19])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 27696403-Amino-2-bromo-5-chloropyridine

生成物 1

HCID 57942301N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a stirred solution of 2-bromo-5-chloro-pyridin-3-ylamine (2.07 g, 10.0 mmol) in anhydrous pyridine (20 mL) was added 3-(trifluoromethyl)benzenesulfonyl chloride (4.90 g, 20.0 mmol) and the progress of the reaction was followed by LCMS. The reaction mixture was stirred overnight (18 h), then concentrated to dryness. The residue was dissolved in THF (20 mL) and stirred 18 h with 1M TBAF (20 mL) in THF to cleave the bis-sulfonamide. The THF was subsequently evaporated and the residue was dissolved in ethyl acetate. The organic phase was then washed with water (2×100 mL), brine, and then dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate-hexane to provide N-(2-Bromo-5-chloro-pyridin-3-yl)-3-trifluoromethyl-benzenesulfonamide as a white crystalline solid. MS m/z 417.1 (M+H).

後処理

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in THF (20 mL)
  3. stirringstirred 18 h with 1M TBAF (20 mL) in THF
  4. customThe THF was subsequently evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic phase was then washed with water (2×100 mL), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-344b9f36815242df980eecd1cde84ba6
出典データセット
uspto-grants-2012_01
特許番号
US08093247B2

関連ノート

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