Benzenesulfonyl chloride → HCID 67227783, compound

HRID 1515912Notes

Reaction equation

HRID 1515912 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.[OH-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:16]1([S:22]([N:9]2[C:6]3=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:4]=[C:5]3[CH:11]=[CH:10]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 307721175-Trifluoromethyl-1H-Pyrrolo[2,3-B]Pyridine

Product 1

HCID 67227783HCID 67227783, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (7.5 g, 40.3 mmol), sodium hydroxide (4.84 g, 120.9 mmol) and tetrabutylammonium bromide (390 mg, 1.21 mmol) in dichloromethane (150 mL) at 0° C. was added benzenesulfonyl chloride (10.64 g, 60.45 mmol) dropwise. After stirring for 12 h at room temperature, washed with water (2×30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% dichloromethane/hexanes) to afford 1-benzenesulfonyl-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (6.35 g, 48%): LC/MS m/e calcd for C14H9F3N2O2S [M+H]+ 327.30, observed 326.8.

Workup

  1. washwashed with water (2×30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-76cdb540dbac4b7f96b89673b98e8c5e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…