Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 2197423ノート

反応式

HRID 2197423 の反応式
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12](=[O:18])[NH:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:21]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12]([O:18][CH3:21])=[N:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 6328Methyl iodideHCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

生成物 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate収率 82.2%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 6212Chloroform溶媒

実験手順

(5-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-carbamic acid benzyl ester (3.68 g, 9.94 mmol) was dissolved in chloroform (50 mL) at room temperature under nitrogen in the dark (foil wrapped). Silver carbonate (3.70 g, 13.2 mmol) was added followed by iodomethane (6.2 mL, 99.4 mmol). The reaction mixture was allowed to stir at room temperature for 48 hours. The silver salts were removed by filtration through a pad of celite, washing with more chloroform and the filtrate concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a white solid (3.14 g, 82% yield). MS (ES+) m/e=385. 1H NMR (CDCl3) δH 3.97 (3H, s), 5.23 (2H, s), 7.15 (1H, br s), 7.35-7.47 (5H, m), 8.00 (1H, s), 8.64 (1H, br s).

後処理

  1. customThe silver salts were removed by filtration through a pad of celite
  2. washwashing with more chloroform
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-acd8390d30f74b01bb19a17820dd83ac
出典データセット
uspto-grants-2012_12
特許番号
US08338597B2

反応ノート

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