4-Toluenesulfonyl chloride → N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide

HRID 16422노트

반응식

HRID 16422 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12)[NH2:5].[H-].[Na+].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=2)(=[O:29])=[O:28])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[CH:17]=[CH:18][C:11]=12

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

생성물 1

HCID 17979281N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

147 mg (0.60 mmol) of the compound from example XIX are dissolved in 10 ml of THF, 48 mg (1.21 mmol) of sodium hydride (in THF) are added and the mixture is then stirred at RT for one hour. 242 mg (1.27 mmol) of p-toluenesulfonyl chloride are then added, and the reaction solution is stirred at 60° C. for another hour. The suspension is filtered through CELITE (diatomaceous earth), the filtercake is washed with THF and a little DCM/methanol 10:1 and the filtrate is concentrated using a rotary evaporator. The residue in the flask is taken up in DMSO and purified by RP-HPLC chromatography (gradient: acetonitrile/water).

후처리

  1. stirringthe reaction solution is stirred at 60° C. for another hour
  2. filtrationThe suspension is filtered through CELITE (diatomaceous earth)
  3. washthe filtercake is washed with THF
  4. concentrationa little DCM/methanol 10:1 and the filtrate is concentrated
  5. customa rotary evaporator
  6. custompurified by RP-HPLC chromatography (gradient: acetonitrile/water)

출처 및 근거

ORD 기록
ord-fdb9542229394523b5fb43953e8eac74
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

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