5-Bromo-2-methoxybenzene-1-sulfonyl chloride → HCID 11614188, compound

HRID 730236Notes

Reaction equation

HRID 730236 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16].[Br:25][C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:31]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([S:32]([NH:1][C:2]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=3)[CH:5]=[CH:4][C:3]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)(=[O:16])=[O:17])(=[O:33])=[O:34])[CH:31]=1

Participants

5

Reactant 2

HCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 68950992HCID 68950992, compound

Product 1

HCID 11614188HCID 11614188, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-amino-4-pyridin-4-ylphenyl)-4-chlorobenzene sulfonamide (0.1 mmol) in pyridine (0.5 mL), 5-bromo-2-methoxy-benzenesulfonyl chloride (0.12 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and then was diluted with ethyl acetate (10 mL). The contents were washed with brine (10 mL), dried over sodium sulfate, and concentrated under vacuum. The residue obtained was purified by column chromatography eluting with hexanes/ethyl acetate (1:1) followed by ethyl acetate to give 49 mg of 5-bromo-N-[2-(4-chlorobenzenesulfonylamino) -5-pyridin-4-ylphenyl]-2-methoxybenzenesulfonamide. LC: Tr 0.94 min, MS: 610.8 (M+1)+.

Workup

  1. washThe contents were washed with brine (10 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1adc025a969044bbbdd2eba7f554eb48
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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