3-Amino-2-bromo-5-chloropyridine → N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-3-trifluoromethyl-benzenesulfonamide

HRID 418990

反応式

HRID 418990 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[Br:16][C:17]1[C:22]([NH2:23])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=1>N1C=CC=CC=1>[Br:16][C:17]1[C:22]([NH:23][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:12]([F:15])([F:14])[F:13])[CH:4]=2)(=[O:10])=[O:9])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=1

参加物

4

反応物 2

HCID 27696403-Amino-2-bromo-5-chloropyridineHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride

生成物 1

HCID 57942594N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-3-trifluoromethyl-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (1.5 g, 5.3 mmol) and 2-bromo-5-chloro-pyridin-3-ylamine (500 mg, 2.4 mmol) dissolved in pyridine (20 mL) was heated at 60° C. for 16 h. The solvent was evaporated and the residue suspended in a 1:1 mixture of 2 M NaOH and methanol (20 mL) and heated at 70° C. for 30 min. The methanol was evaporated under reduced pressure and the residue diluted with 15 mL water. The solution was cooled on ice bath and the pH was adjusted to 3 by drop wise addition of concentrated HCl. The solid formed was collected by filtration and the product was purified by flash chromatography on silica gel column to afford the desired product. MS m/z: 450.8 (M+H).

後処理

  1. customThe solvent was evaporated
  2. additionthe residue suspended in a 1:1 mixture of 2 M NaOH and methanol (20 mL)
  3. temperatureheated at 70° C. for 30 min
  4. customThe methanol was evaporated under reduced pressure
  5. additionthe residue diluted with 15 mL water
  6. temperatureThe solution was cooled on ice bath
  7. additionthe pH was adjusted to 3 by drop wise addition of concentrated HCl
  8. customThe solid formed
  9. filtrationwas collected by filtration
  10. customthe product was purified by flash chromatography on silica gel column

出典と根拠

ORDレコード
ord-bdf7097ebde54bb28fa3f5be240f6d06
出典データセット
uspto-grants-2012_01
特許番号
US08093247B2

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