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

HRID 16422Notes

Reaction equation

HRID 16422 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fdb9542229394523b5fb43953e8eac74
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…