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4-Toluenesulfonyl chloride → 6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine

HRID 1695736
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HRID 1695736 반응식
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH:12]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]2[CH:8]=[N:9][N:10]([S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[C:11]=2[CH:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chloride2회HCID 24758Sodium hydride2회HCID 247280636-Bromo-1H-indazol-4-amine

생성물 1

HCID 582557476-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-amine수율 51.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
0 °C

실험 절차

To a suspension of sodium hydride (5.66 g) in anhydrous DMF (75 ml) stirring at 0° C. was added a solution of 6-bromo-1H-indazol-4-amine (30 g), also in anhydrous DMF (125 ml), dropwise. The reaction mixture was stirred for 1 h at 0° C. then a solution of 4-methylbenzenesulfonyl chloride (27 g) in anhydrous DMF (100 ml) was added dropwise. The reaction was stirred for 2 h. A further portion of sodium hydride (0.57 g) was added followed by 4-methylbenzenesulfonyl chloride (2.70 g). The reaction mixture was left to stand overnight at room temperature, before pouring onto ice/water (1800 ml). A precipitate formed that was collected by filtration, tritrurated using diethyl ether:methanol (1:1, v/v), then re-collected by filtration and dried in vacuo at 40° C. over the weekend to give title compound, (26.5 g).

후처리

  1. stirringThe reaction mixture was stirred for 1 h at 0° C.
  2. stirringThe reaction was stirred for 2 h
  3. waitThe reaction mixture was left
  4. additionbefore pouring onto ice/water (1800 ml)
  5. customA precipitate formed
  6. filtrationthat was collected by filtration
  7. filtrationv/v), then re-collected by filtration
  8. customdried in vacuo at 40° C. over the weekend

출처 및 근거

ORD 기록
ord-70d3597a41f54a258877d0a2f807cb61
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163743B2

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