Pyridine → HCID 67243569, compound

HRID 1370482Notes

Reaction equation

HRID 1370482 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([NH2:23])=[CH:18][C:17]=1[Cl:24])=[CH:8]2)=[O:4].[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([O:15][C:16]1[C:17]([Cl:24])=[CH:18][C:19]([NH:23][S:33]([C:27]3[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=3[Cl:25])(=[O:35])=[O:34])=[CH:20][C:21]=1[Cl:22])=[CH:8]2)=[O:4]

Participants

5

Reactant 4

HCID 1049PyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 516892Sodium BicarbonateHCID 57440938HCID 57440938, compound

Product 1

HCID 67243569HCID 67243569, compoundYield 44.5%

Procedure

A solution of 3-(4-amino-2,6-dichloro-phenoxy)-quinoline-6-carboxylic acid methyl ester (96) (0.93 mmol) and 2,4-dichlorobenzenesulfonyl chloride (250 mg, 1.02 mmol) in pyridine (0.13 mL, 1.53 mmol) CH2Cl2 (3.7 mL) was stirred at room temperature for 12 h. Sat NaHCO3 was added to the reaction mixture, which was then extracted twice with AcOEt. Organic layer was washed by brine, dried over anhydrous MgSO4, and concentrated. Crude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel) to afford compound 45 (237 mg, 41%, in 3 steps).

Workup

  1. extractionwas then extracted twice with AcOEt
  2. washOrganic layer was washed by brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customCrude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel)

Sources & evidence

ORD record
ord-85c7f2da2d7743e9a647cf7f82e5693e
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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