2,4-Difluorobenzenesulfonyl Chloride → N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide

HRID 520522

反応式

HRID 520522 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][S:19]([C:13]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=2[F:11])(=[O:21])=[O:20])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 447548695-Bromo-2-methoxypyridin-3-amine

生成物 1

HCID 59859951N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide収率 5.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a cooled (0° C.) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 mL). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with 70 ml of methylene chloride, and dried in a vacuum oven at 50° C. to give the title compound (15

後処理

  1. custom(reaction became heterogeneous)
  2. customThe ice bath was removed
  3. customMost of the pyridine was removed in vacuo
  4. additionthe residue diluted with water (500 mL)
  5. filtrationThe solids were filtered off
  6. washwashed with copious amounts of water
  7. customto give 21 g of crude desired product
  8. filtrationwas filtered
  9. washwashed with water

出典と根拠

ORDレコード
ord-687bf00e3e2b48c0a1a66cf5f9b36fe5
出典データセット
uspto-grants-2016_05
特許番号
US09326987B2

関連ノート

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