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

HRID 16422ノート

反応式

HRID 16422 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fdb9542229394523b5fb43953e8eac74
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

反応ノート

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