Iodine chloride → 4-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

HRID 79029ノート

反応式

HRID 79029 の反応式
[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([Si](C)(C)C)=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:29]Cl>C(Cl)Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[S:15][N:14]=[CH:13][C:12]=2[C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:29])=[CH:20][C:19]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 24640Iodine chlorideHCID 670835784-(2-Fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester

生成物 1

HCID 670836334-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester収率 98%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 24477Sodium Thiosulfate溶媒

反応条件

温度
-78 °C

実験手順

To a solution 4-(2-fluoro-4-trimethylsilanyl-phenylamino)-benzo[d]isothiazole-5-carboxylic acid tert-butyl ester (416 mg, 1.0 mmol) in DCM (10 mL) at −78° C. was added iodine monochloride as a solution in DCM (2.0 mL, 1M, 2.0 mmol). The reaction mixture was stirred at −78° C. for 1 hour then diluted with saturated aqueous sodium thiosulfate solution and extracted with DCM. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to yield the title compound as a yellow foam (459 mg, 98%). LCMS (Method B): RT=5.32 min, [M+H]+=471.

後処理

  1. extractionextracted with DCM
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2ff70ac5481048b68eb181435c44d288
出典データセット
uspto-grants-2014_09
特許番号
US08841462B2

反応ノート

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