Methyl iodide → N-(6-methoxy-5-methylpyridin-2-yl)acetamide

HRID 1772912ノート

反応式

HRID 1772912 の反応式
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[N:6]=1)(=O)C.IC>CO.C(Cl)Cl>[CH3:1][O:4][C:5]1[N:6]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[CH3:11]

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 900222806-Acetamido-3-methylpyridin-2-yl acetate2 回

生成物 1

HCID 90030978N-(6-methoxy-5-methylpyridin-2-yl)acetamide収率 143.6%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
35 °C

実験手順

To a stirred solution of 6-acetamido-3-methylpyridin-2-yl acetate (3.44 g, 16.5 mmol) in 2:1 MeOH/DCM (105 mL) at rt was added Ag2CO3 (9.11 g, 33.0 mmol) followed by iodomethane (3.09 mL, 49.6 mmol). The resulting mixture was stirred at 35° C. for 18 h then stood at rt for 2 d. The reaction mixture was combined with 2 previous batches derived from 6-acetamido-3-methylpyridin-2-yl acetate (590 mg, 2.83 mmol and 3.44 g, 16.5 mmol) and the combined batches were filtered through celite, rinsing with DCM. After concentration of the filtrate in vacuo purification by gradient column chromatography eluting with 20-50% EtOAc in heptane yielded the title compound (4.27 g, 23.7 mmol) as a white solid.

後処理

  1. waitthen stood at rt for 2 d
  2. filtrationthe combined batches were filtered through celite
  3. washrinsing with DCM
  4. customAfter concentration of the filtrate in vacuo purification by gradient column chromatography
  5. washeluting with 20-50% EtOAc in heptane

出典と根拠

ORDレコード
ord-3b6825dd39994299baeddc5f38fe9686
出典データセット
uspto-grants-2016_02
特許番号
US09249160B2

反応ノート

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