Methyl iodide → HCID 118021625、化合物

HRID 575591ノート

反応式

HRID 575591 の反応式
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[CH3:13]I.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5](=[O:8])[N:6]([CH3:13])[CH:7]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 587031425-Bromo-3,4-dimethylpyridin-2(1H)-one

生成物 1

HCID 118021625HCID 118021625、化合物収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-bromo-3,4-dimethyl-1H-pyridin-2-one (402.0 mg, 2.0 mmol) in anhydrous THF (20 mL) was added NaH (96.0 mg, 2.4 mmol). The resulting mixture was stirred at 0° C. for 30 min. Methyl iodide (568.0 mg, 4.0 mmol) was added and the reaction was stirred at 32° C. for 3 h. Then, saturated aqueous NH4Cl (100 mL) was added and the mixture extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE:EA=10:1 to 2:1) to give the title compound (350.0 mg, 80%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.38 (s, 1H), 3.52 (s, 3H), 2.27 (s, 3H), 2.20 (s, 3H). LCMS (M+H)+ 216.

後処理

  1. stirringthe reaction was stirred at 32° C. for 3 h
  2. extractionthe mixture extracted with ethyl acetate (100 mL×3)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (PE:EA=10:1 to 2:1)

出典と根拠

ORDレコード
ord-cd7649705d8a40c8912d9f207b435ee2
出典データセット
uspto-grants-2015_05
特許番号
US09034900B2

反応ノート

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