3-Amino-2-bromopyridine → N-(2-Bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

HRID 1716278Notes

Reaction equation

HRID 1716278 reaction equation
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[O:9]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[C:7]([NH:8][S:22]([C:19]2[CH:18]=[CH:17][C:16]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:21][CH:20]=2)(=[O:24])=[O:23])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6428163-Amino-2-bromopyridineHCID 27947564-Phenoxybenzene-1-sulfonyl chloride

Product 1

HCID 86619931N-(2-Bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-3-aminopyridine (0.69 g, 3.98 mmol) in dry pyridine (15 mL) was added a solution of 4-phenoxy-benzenesulfonyl chloride (1.03 g, 3.98 mmol) in pyridine (3 mL) at 0 C. The resulting mixture was allowed to warm to room temperature and stirred until TCL showed the completion of the reaction. The reaction mixture was diluted with EtOAc and washed with aqueous HCl solution. After the pyridine was neutralized, the organics were washed with water, brine and dried over anhydrous Na2SO4. The filtration (Celite) and concentration under vacuo gave a crude material, which was purified by silica column (30% EtOAc/hexanes). MS: 405, 407 (M+H)+.

Workup

  1. customthe completion of the reaction
  2. washwashed with aqueous HCl solution
  3. washthe organics were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThe filtration (Celite) and concentration under vacuo

Sources & evidence

ORD record
ord-99832a85e0594d09a1aea2a4c5c5925d
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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