Sodium Sulfite → Methyl 4-amino-3-chloro-6-(2,5-difluoro-4-iodophenyl)-5-fluoropicolinate

HRID 516565

反応式

HRID 516565 の反応式
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([Si](C)(C)C)=[CH:11][C:10]=2[F:20])[N:5]=[C:4]([C:21]([O:23][CH3:24])=[O:22])[C:3]=1[Cl:25].[I:26]Cl.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([I:26])=[CH:11][C:10]=2[F:20])[N:5]=[C:4]([C:21]([O:23][CH3:24])=[O:22])[C:3]=1[Cl:25]

参加物

5

反応物 3

HCID 24437Sodium SulfiteHCID 24640Iodine chlorideHCID 90409474Methyl 4-amino-3-chloro-6-(2,5-difluoro-4-(trimethylsilyl)phenyl)-5-fluoropicolinate

生成物 1

HCID 90409448Methyl 4-amino-3-chloro-6-(2,5-difluoro-4-iodophenyl)-5-fluoropicolinate収率 74.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

To a solution of methyl 4-amino-3-chloro-6-(2,5-difluoro-4-(trimethylsilyl)phenyl)-5-fluoropicolinate (0.280 g, 0.720 mmol) in CH2Cl2 (2.88 mL) at 20° C. was added iodine monochloride (0.144 mL, 2.880 mmol). The reaction mixture was stirred at 20° C. overnight. The mixture was then poured into a 10% aqueous solution of Na2SO3, extracted with EtOAc (3×), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound as a white solid (0.237 g, 0.536 mmol, 74.4%).

後処理

  1. extractionextracted with EtOAc (3×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (SiO2, hexanes/EtOAc gradient)

出典と根拠

ORDレコード
ord-25645352d02d493fb79f4cae7e88543c
出典データセット
uspto-grants-2015_08
特許番号
US09113629B2

関連ノート

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