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

HRID 2427189노트

반응식

HRID 2427189 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c3b2a5be2654f8da7b9216d170a6a5b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968567B2

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