Methyl iodide → N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

HRID 1623508ノート

反応式

HRID 1623508 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:18])[S:10]([CH2:13][CH3:14])(=[O:11])=[O:12])[CH:5]=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

生成物 1

HCID 66788309N-((5-Bromopyridin-3-yl)methyl)-N-methylethanesulfonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (0.21 g, 0.752 mmol), prepared as described in Example 11a, in DMF (6 mL) at −10° C., was added sodium hydride (60% oil dispersion, 39 mg, 0.98 mmol). The reaction was stirred for 15 minutes at which time iodomethane (0.056 ml, 0.903 mmol) dissolved in DMF (1 mL) was added. The reaction was stirred at −10° C. for an additional 15 minutes and was then quenched with ammonia hydroxide (2 mL). The reaction was diluted with brine and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-methyl-amide; MS: (ES+) m/z 293.1 (M+H)+.

後処理

  1. additionwas added
  2. customwas then quenched with ammonia hydroxide (2 mL)
  3. additionThe reaction was diluted with brine
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate, 0 to 80%)

出典と根拠

ORDレコード
ord-2d4081b673b441b7af240259066e3c9e
出典データセット
uspto-grants-2014_07
特許番号
US08778972B2

反応ノート

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