Cesium carbonate → 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 75992

反応式

HRID 75992 の反応式
Br[C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1.[N+:23]([C:26]1[CH:27]=[N:28][NH:29][CH:30]=1)([O-:25])=[O:24].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.[Cu](I)I.O.C(OCC)(=O)C>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:7]2[C:2]([N:28]3[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:30]=[N:29]3)=[N:3][CH:4]=[C:5]([Cl:22])[CH:6]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 57942597N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide

生成物 1

HCID 684640854-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzene sulfonamide (534 mg, 1.32 mmol), 4-nitropyrazole (224 mg, 1.98 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (42 μL, 0.264 mmol), copper iodide (51 mg, 0.264 mmol), and cesium carbonate (903 mg, 2.77 mmol) in 5 mL of N,N-dimethylacetamide was heated at 130° C. for 2 hours. Ethyl acetate and water were added and the layers were separated. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes) to afford 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide as a white solid.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-f9f0f6399497473a809f2b5cef77dd9d
出典データセット
uspto-grants-2014_09
特許番号
US08835468B2

関連ノート

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