Benzyl Bromide → N-Benzyl-N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

HRID 1716279Notes

Reaction equation

HRID 1716279 reaction equation
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:31]([N:8]([C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86619931N-(2-Bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

Product 1

HCID 86619932N-Benzyl-N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzene-sulfonamide (0.38 g, 0.94 mmol) from step A and K2CO3 (0.39 g, 2.81 mmol) in dry DMF (10 mL) was added benzylbromide (0.13 mL, 1.13 mmol). The resulting mixture was heated at 80 C overnight. The cooled reaction was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc (×3) and the combined organics were washed with water and brine, dried over anhydrous Na2SO4, and filtered through Celite. The filtrate was concentrated under the reduced pressure and purified by chromatography (silica gel, 25% EtOAc/hexanes). MS: 495, 497 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated at 80 C overnight
  2. customThe cooled reaction
  3. extractionThe aqueous layer was extracted with EtOAc (×3)
  4. washthe combined organics were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate was concentrated under the reduced pressure
  8. custompurified by chromatography (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a5e6b819d4894836bc7d8f888827d806
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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