4-Toluenesulfonyl chloride → HCID 58158533, compound

HRID 2095764Notes

Reaction equation

HRID 2095764 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([F:26])[CH:10]=2)=[CH:4][CH:3]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1>[F:26][C:11]1[CH:10]=[C:9]([O:8][C:5]2[CH:6]=[N:7][C:2]([NH:1][S:33]([C:30]3[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=3)(=[O:35])=[O:34])=[CH:3][CH:4]=2)[CH:14]=[CH:13][C:12]=1[NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 58158590HCID 58158590, compound

Product 1

HCID 58158533HCID 58158533, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl {4-[(6-aminopyridin-3-yl)oxy]-2-fluorophenyl}carbamate (32 g, 90.6 mmol) in pyridine (141 mL) was added p-toluenesulfonyl chloride (18.3 g, 108.7 mmol), and the mixture was stirred at 80° C. for 3 hr. After cooling to room temperature, pyridine was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate and collected by filtration to give the title compound (32.0 g, 70%).

Workup

  1. temperatureAfter cooling to room temperature
  2. custompyridine was evaporated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. washthe residue was washed with hexane/ethyl acetate
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4140ad7557cf4e348bae1f20e8392317
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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