Pyridine → 2',4'-Difluoro-N-(3-vinylphenyl)biphenyl-4-sulfonamide

HRID 221390Notes

Reaction equation

HRID 221390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH2:6].[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[CH2:6])[CH:3]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 42600413-AminostyreneHCID 448910942',4'-Difluoro-biphenyl-4-sulfonyl chloride

Product 1

HCID 673295122',4'-Difluoro-N-(3-vinylphenyl)biphenyl-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino styrene (1.36 g, 11.4 mmol) was added to a solution of 2′,4′-difluorobiphenyl-4-sulphonyl chloride (3.0 g, 10.3 mmol) in DCM (25 mL) at 0° C. Pyridine (6.0 mL, 74 mmol) was then added and the mixture was allowed to stir and warm to room temperature overnight. The reaction was partitioned between further DCM (100 mL) and 2 M HCl (30 mL), stirred and separated. The DCM layer was washed with water (20 mL) and brine (20 mL) and dried over MgSO4. The solvent was evaporated and the title compound obtained as an orange gum (3.46 g) which was used without further purification.

Workup

  1. customThe reaction was partitioned between further DCM (100 mL) and 2 M HCl (30 mL)
  2. stirringstirred
  3. customseparated
  4. washThe DCM layer was washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8693603b47e44612be3d8ea5329897b9
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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