Pyridine → 5-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide

HRID 1049020ノート

反応式

HRID 1049020 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.N1C=CC=CC=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:10])=[O:9])=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 185437114-Fluoro-N-(2-methylpropyl)anilineHCID 445580975-Bromopyridine-2-sulfonyl chloride

生成物 1

HCID 867218735-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide収率 82.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 5-bromo-pyridine-2-sulfonyl chloride (330 mg, 1.29 mmol) in DCM (10 mL) was added pyridine (208 μL, 2.57 mmol) followed by a solution of (4-fluoro-phenyl)-isobutyl-amine (215 mg, 1.29 mmol) in DCM (10 mL) and the reaction was stirred at room temperature for 16 hours. Water and saturated aqueous NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAc in cyclohexane) to give 5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (414 mg, 78%). LCMS (m/z, Method A) ES+ 387/389 [M+1]+.

後処理

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated
  4. customthen purified by silica gel column chromatography (0-20% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-1f6acb0786c34e3ca8862c8391a899d9
出典データセット
uspto-grants-2016_07
特許番号
US09382222B2

反応ノート

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