1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594118ノート

反応式

HRID 594118 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:21](N=C(N(C)C)N(C)C)([CH3:24])([CH3:23])[CH3:22].BrCC(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:22][CH:21]([CH3:24])[CH3:23])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898759264-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

生成物 1

HCID 898760314-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide収率 24.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
150 °C

実験手順

4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (400 mg, 1.359 mmol) was dissolved in acetonitrile (4 mL), 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (284 μL, 1.36 mmol) added and the mixture stirred for 20 minutes. 1-Bromo-2-methylpropane (296 μL, 2.72 mmol) was then added and the reaction vessel sealed and heated by microwaves to 150° C. for 1 hour. The reaction was cooled and concentrated in vacuo, then the crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (117 mg). LCMS (2 min, formic) Rt 1.38 min, m/z (ES+) 351 (M+H).

後処理

  1. customthe reaction vessel sealed
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. extractionthe crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water
  5. concentrationconcentrated in vacuo
  6. custompurified by mass

出典と根拠

ORDレコード
ord-4eff40853b694a468954a70c0604116c
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

反応ノート

読み込み中…