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

HRID 2427189ノート

反応式

HRID 2427189 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7c3b2a5be2654f8da7b9216d170a6a5b
出典データセット
uspto-grants-2011_06
特許番号
US07968567B2

反応ノート

読み込み中…