1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

HRID 594106ノート

反応式

HRID 594106 の反応式
C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:14][CH:15]([CH3:17])[CH3:16].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(#N)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760604-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide

生成物 1

HCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide収率 63.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
150 °C

実験手順

A mixture of 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.121 ml, 0.581 mmol), 1-bromo-2-methylpropane (0.126 ml, 1.162 mmol) and 4-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide (164 mg, 0.581 mmol) was prepared and dissolved in acetonitrile (4 mL). The reaction was heated by microwaves to 150° C. for 30 minutes, then again for a further 15 minutes. After cooling the reaction was quenched with sodium hydroxide in ethanol and concentrated in vacuo. The product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid. The organic phase was dried by passing through a hydrophobic frit, concentrated in vacuo and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient), to give the title compound (125.5 mg). LCMS (2 min, formic) Rt 1.33 min, m/z (ES+) 339 (M+H).

後処理

  1. customwas prepared
  2. temperatureAfter cooling the reaction
  3. customwas quenched with sodium hydroxide in ethanol
  4. concentrationconcentrated in vacuo
  5. extractionThe product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. custompurified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)

出典と根拠

ORDレコード
ord-3f58bd877713435fa7f3c4434428414a
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…