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

HRID 520522

반응식

HRID 520522 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-687bf00e3e2b48c0a1a66cf5f9b36fe5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326987B2

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