Pyridine → 3-[2,6-Dichloro-4-(2,4-dichloro-benzenesulfonylamino)-phenoxy]-quinoline-8-carboxylic acid methyl ester

HRID 2427189Notes

Reaction equation

HRID 2427189 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([NH2:23])=[CH:18][C:17]=1[Cl:24])=[CH:10]2)=[O:4].N1C=CC=CC=1.[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[S:39](Cl)(=[O:41])=[O:40].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:17]([Cl:24])=[CH:18][C:19]([NH:23][S:39]([C:33]3[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:32]=3[Cl:31])(=[O:41])=[O:40])=[CH:20][C:21]=1[Cl:22])=[CH:10]2)=[O:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 516892Sodium BicarbonateHCID 574409393-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester

Product 1

HCID 672429863-[2,6-Dichloro-4-(2,4-dichloro-benzenesulfonylamino)-phenoxy]-quinoline-8-carboxylic acid methyl esterYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester (315) (1.26 mmol) in Pyridine (0.15 ml, 1.80 mmol) and CH2Cl2 (5 ml), was added 2,4-Dichlorobenzenesulfonyl chloride (381 mg, 1.55 mmol). The mixture was stirred at room temperature for 12 hr. Sat NaHCO3 was added to the reaction mixture, which was then extracted twice with AcOEt. Organic layer was washed by Brine, dried over MgSO4, and concentrated. The crude residue was purified by column chromatography (Hexane/AcOEt=2/1, 80 g of silica gel) to afford compound 182 (506 mg, 70%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-7c3b2a5be2654f8da7b9216d170a6a5b
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

Loading…