Isobutyl iodide → methyl 2-chloro-4-(N-isobutylmethylsulfonamido)benzoate

HRID 1364761ノート

反応式

HRID 1364761 の反応式
I[CH2:2][CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:12][C:13]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>CN(C=O)C>[Cl:12][C:13]1[CH:22]=[C:21]([N:23]([CH2:2][CH:3]([CH3:5])[CH3:4])[S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

参加物

5

反応物 3

HCID 10556Isobutyl iodideHCID 10796Cesium carbonateHCID 54238017Methyl 2-chloro-4-(methylsulfonamido)benzoate

生成物 1

HCID 66877616methyl 2-chloro-4-(N-isobutylmethylsulfonamido)benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

175 μL of 1-iodo-2-methylpropane and 740 mg of Cesium Carbonate were added to 200 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in 2 mL of DMF and stirred in the microwave at 140° C. for 30 minutes. The reaction mixture was extracted in Ethyl Acetate twice with water, dried over Magnesium Sulfate, filtered, concentrated and purified on ISCO Combi-Flash to give methyl 2-chloro-4-(N-isobutylmethylsulfonamido)benzoate. 120 mg of methyl 2-chloro-4-(N-isobutylmethylsulfonamido)benzoate was hydrolyzed via Procedure M to yield 110 mg of crude 2-chloro-4-(N-isobutylmethylsulfonamido)benzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 2-chloro-4-(N-isobutylmethylsulfonamido)benzoic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(N-isobutylmethylsulfonamido)benzamide. MS (Q1) 492 (M)+.

後処理

  1. extractionThe reaction mixture was extracted in Ethyl Acetate twice with water
  2. dry with materialdried over Magnesium Sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on ISCO Combi-Flash

出典と根拠

ORDレコード
ord-0cecce1a3b9f4d189bc7b23e886999e6
出典データセット
uspto-grants-2011_02
特許番号
US07888364B2

反応ノート

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