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1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

HRID 594114
ノート
印刷プレビュー

反応式

HRID 594114 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:21])[CH3:20])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:22](N=C(N(C)C)N(C)C)([CH3:25])([CH3:24])[CH3:23].BrCC(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:23][CH:22]([CH3:25])[CH3:24])[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:21])[CH3:20])=[CH:14][N:13]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898763764-fluoro-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

生成物 1

HCID 898761814-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide収率 48.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-fluoro-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide (127 mg, 0.41 mmol) was dissolved in acetonitrile (3 mL) and to this solution was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.09 mL, 0.41 mmol). The mixture was allowed to stir at room temperature for 30 minutes, 1-bromo-2-methylpropane (0.09 mL, 0.83 mmol) was then added to the mixture and the reaction vessel sealed and heated by microwaves to 150° C. for 1 hour. The reaction mixture was concentrated in vacuo and the crude product extracted to the organic phase of an aqueous workup between ethyl acetate and water. The organic phase was then passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (73 mg). LCMS (2 min, formic) Rt 1.44 min, m/z (ES+) 365 (M+H).

後処理

  1. customthe reaction vessel sealed
  2. temperatureheated by microwaves to 150° C. for 1 hour
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionthe crude product extracted to the organic phase of an aqueous workup between ethyl acetate and water
  5. concentrationconcentrated in vacuo
  6. custompurified by mass

出典と根拠

ORDレコード
ord-410d0e22a4714b398548ff9d09b6ee0c
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242972B2

反応ノート

読み込み中…

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